反応 #81457

反応方程式

EtOAc

NaCl

t-butyl 4-(acetoxymethyl)-3-nitrobenzoate

hydrazine hydrate

→

t-Butyl 4-(hydroxymethyl)-3-nitrobenzoate

収率 93.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他the organic layer collected
2. 2
   workup.STIRRINGafter shaking
3. 3
   洗浄The organic layer was washed further with saturated aq. NaCl (2×85 mL)
4. 4
   乾燥dried (MgSO4)
5. 5
   その他Removal of volatiles in vacuo
6. 6
   その他gave the product in 93% yield as yellow crystals

実験手順

To a solution of 14.1 g (47.7 mmol, 1.00 eq.) of t-butyl 4-(acetoxymethyl)-3-nitrobenzoate in MeOH (200 mL) was added 27.0 mL (477 mmol, 10.0 eq.) of hydrazine hydrate (55% hydrazine). The resulting yellow solution was stirred at 25° C. for 4 hr. EtOAc (250 mL) and saturated aq. NaCl (85 mL) were added, and the organic layer collected after shaking. The organic layer was washed further with saturated aq. NaCl (2×85 mL), and then dried (MgSO4). Removal of volatiles in vacuo gave the product in 93% yield as yellow crystals. The reaction is represented in Scheme 5.

出典