Trifluoroacetic acid → 2-(4-Methoxybenzyl)benzo[b]thiophene

HRID 234395Notes

Reaction equation

HRID 234395 reaction equation
[S:1]1[C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5]2[S:1][C:2]3[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=3[CH:4]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 49962600a-(2-Benzo[b]thienyl)-4-methoxybenzyl alcohol

Product 1

HCID 229983842-(4-Methoxybenzyl)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-methoxybenzyl)-benzo[b]thiophene was prepared by the method of Example 47B with α-(2-benzo[b]thienyl)-4-methoxybenzyl alcohol (1.9 mmoles) 0.50 g), triethylsilane (2.0 mmoles, 0.32 mls), CH2Cl2 (20 ml) and TFA (3.7 mmoles, 0.30 ml). Recrystallization with hexanes and chloroform provided 0.40 (85%) of a pink solid.

Workup

  1. customRecrystallization with hexanes and chloroform

Sources & evidence

ORD record
ord-3b3cda7d8e884231b345371b57556f30
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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