Triphenylphosphine → 4-(2-Chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene

Triphenylphosphine (3.94 g, 15 mmol) is added to a solution of 2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethanol (2.74 g, 15 mmol) in Cl4C/Acetonitrile 1:1 (20 mL) at room temperature and the mixture is maintained under stirring for 3 hours monitoring the reaction by TLC. The solution is concentrated to half the volume at reduced pressure, CH2Cl2 is added and washed with water. The organic phase is separated and evaporated to dryness. The crude is treated with diethyl ether and the precipitate is filtered. The diethyl ether is evaporated to dryness, and the resulting crude is purified by column chromatography, giving 4-(2-chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene (1.7 g, 8.4 mmol, 56%, oil). 1H NMR (300 MHz, CDCl3): δ 1.54 (m, 1H), 1.79 (m, 1H), 1.92 (m, 3H), 2.20 (m, 1H), 2.77 (m, 2H), 3.00 (m, 1H), 3.64 (m, 2H), 6.86 (d, J=5.2 Hz, 1H), 7.06 (d, J=5.2 Hz, 1H).

1. temperaturethe mixture is maintained
2. customthe reaction by TLC
3. concentrationThe solution is concentrated to half the volume at reduced pressure, CH2Cl2
4. additionis added
5. washwashed with water
6. customThe organic phase is separated
7. customevaporated to dryness
8. additionThe crude is treated with diethyl ether
9. filtrationthe precipitate is filtered
10. customThe diethyl ether is evaporated to dryness
11. customthe resulting crude is purified by column chromatography

ORDレコード

ord-64ec361d5ec847a793a347187d21724c

出典データセット

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08227625B2