反应 #68730

反应方程式

3

4-Hydroxylmethyl benzophenone

sodium hydride

allyl bromide

4-Bromomethyl benzophenone

4-Hydroxylmethyl benzophenone

→

4-Bromomethyl benzophenone

9

收率 92.0%

4-(Allyloxymethyl)benzophenone

收率 92.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture as stirred for 18 h. the
2. 2
   其他quenched with water
3. 3
   浓缩concentrated in vacuo
4. 4
   其他the organic layer collected
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated
7. 7
   其他A mineral oil impurity was removed
8. 8
   洗涤eluting with petrol

实验过程

4-Bromomethyl benzophenone (2) was prepared as described in Reference Example 1. 4-Bromomethyl benzophenone (2) was converted into 4-Hydroxylmethyl benzophenone (3) as described in Reference Example 2. To a solution of 3 (0.5 g, 3.4 mmol) in dry THF (10 ml) was added sodium hydride (0.3 g, 60% dispersion in mineral oil, 6.7 mmol). The mixture was stirred for 5 min, then allyl bromide (0.8 g, 6.7 mmol) was added. The mixture as stirred for 18 h. the quenched with water and concentrated in vacuo. The residue was portioned between DCM and water, the organic layer collected, dried over MgSO4 and concentrated. A mineral oil impurity was removed using a silica plug eluting with petrol then ethyl acetate to yield 9 (0.6 g, 92%) as a yellow oil; δH (CDCl3) 4.08 (dt, 2H, J=1.4, 5.5 Hz, OCH2CH═CH2), 4.60 (s, 2H, ArCH2O), 5.24 (ddt 1H, J=1.4, 3.2, 10.3 Hz, OCH2CH═CHH), 5.34 (ddt 1H, J=1.4, 3.2, 17.3 Hz, OCH2CH═CHH), 5.88-6.08 (m, 1H, OCH2CH═CHH), 7.42-7.50 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.54-7.62 (m, 1H, 4′-H), 7.78-7.82 (m, 4H, 2-, 2′-, 6-, 6′-H) ppm; δC (CDCl3) 61.4, 71.3 (ArCH2O, OCH2CH═CH2), 117.3 (OCH2CH═CH2), 127.0, 128.1 (3-, 3′-, 5-, 5′-C), 129.8, 130.1 (2-, 2′-, 6-, 6′-C), 132.2 (4′-C), 134.3 (OCH2CH═CH2), 136.6, 137.5 (1-, 1′-C), 143.1 (4-C), 196.2 (C═O) ppm; νmax (thin film) 3061, 2855, 1658, 1609, 1447, 1412, 1278, 1089, 924 cm−1; m/z (Er) 252 ([M+], 85%), 222 (100%); found 252.1158, C17H16O2 requires 252.1150.

来源