反応 #551203

反応方程式

triphenyl phosphine

1-bromo-4-chlorobenzene

3-buten-1-ol

→

title compound

収率 52.0%

trans-4-(4'-Chlorophenyl)-3-buten-1-ol

収率 52.0%

溶媒

triethylamine

acetonitrile

反応条件

後処理

1. 1
   その他The tube is sealed
2. 2
   温度heated 20 hr longer at 100°-120° C
3. 3
   温度The mixture is cooled
4. 4
   その他partitioned between 300 ml of 2N hydrochloric acid and ether
5. 5
   その他The layers are separated
6. 6
   抽出the aqueous layer is extracted with two additional volumes of ether
7. 7
   洗浄The combined ether extracts are washed with 2×100 ml portions of 2N hydrochloric acid
8. 8
   乾燥dried over sodium sulfate
9. 9
   抽出The filtered ether extract
10. 10
    濃縮is concentrated under vacuum
11. 11
    その他to give 12.7 g of crude product which
12. 12
    その他is purified by chromatography on silica gel

実験手順

To a suspension of triphenyl phosphine (2.1 g, 8.0 mmole) in 300 ml of triethylamine and 30 ml of acetonitrile under nitrogen is added successively palladium (II) acetate (0.45 g, 2.0 mmole), 1-bromo-4-chlorobenzene (19.1 g, 110 mmole) and 3-buten-1-ol (7.21 g, 100 mmole) in a pressure tube. The tube is sealed and heated in an oil bath to 100° C. for 24 hr. The tube is opened under nitrogen, charged with additional palladium (II) acetate, resealed and heated 20 hr longer at 100°-120° C. The mixture is cooled, vented to nitrogen and partitioned between 300 ml of 2N hydrochloric acid and ether. The layers are separated and the aqueous layer is extracted with two additional volumes of ether. The combined ether extracts are washed with 2×100 ml portions of 2N hydrochloric acid and then dried over sodium sulfate. The filtered ether extract is concentrated under vacuum to give 12.7 g of crude product which is purified by chromatography on silica gel using toluene eluent. There is obtained 9.5 g of the title compound. Rf =0.77 (silica gel, toluene).

出典