Trifluoroacetic acid → 2-[3,4-(Methylenedioxy)benzyl]benzo[b]thiophene

HRID 2270620Notes

Reaction equation

HRID 2270620 reaction equation
[S:1]1[C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]3[O:13][CH2:14][O:15][C:9]=3[CH:8]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>>[CH2:14]1[O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]3[S:1][C:2]4[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=4[CH:4]=3)=[CH:8][C:9]=2[O:15]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 49964046a-(2-Benzo[b]thienyl)-3,4-(methylenedioxy)benzyl alcohol

Product 1

HCID 229984072-[3,4-(Methylenedioxy)benzyl]benzo[b]thiophene

Procedure

2-[3,4-(methylenedioxy)benzyl]benzo[b]thiophene was prepared by the method of Example 47B using a-(2-benzo[b]thienyl)-3,4-(methylenedioxy)benzyl alcohol (6.2 mmoles, 1.8 g), triethylsilane (6.8 mmoles, 1.1 ml) CH2Cl2 (50 ml) and TFA (12.4 mmoles, 0.95 ml). Recrystallization from hexanes provided 1.2 g (73%) of a light orange solid.

Workup

  1. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-5ae45cd65b7942f8a074dcb40a5158f7
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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