Benzo(B)Thiophene → a-(2-Benzo[b]thienyl)-3,4-(methylenedioxy)benzyl alcohol

HRID 1738435Notes

Reaction equation

HRID 1738435 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Li]C(C)(C)C.[CH:15]1[C:20]([CH:21]=[O:22])=[CH:19][C:18]2[O:23][CH2:24][O:25][C:17]=2[CH:16]=1>C1COCC1>[S:1]1[C:5]([CH:21]([OH:22])[C:20]2[CH:15]=[CH:16][C:17]3[O:25][CH2:24][O:23][C:18]=3[CH:19]=2)=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 8438PiperonalHCID 178418306HCID 178418306, compound

Product 1

HCID 49964046a-(2-Benzo[b]thienyl)-3,4-(methylenedioxy)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-(2-Benzo[b]thienyl)-3,4-(methylenedioxy)benzyl alcohol was prepared by the method of Example 40A using benzo[b]thiophene (7.5 mmoles, 1.0 g), t-BuLi (1.7 M, 9.7 mmoles, 5.7 ml), piperonal (8.9 mmoles, 1.0 g) and THF (20 ml). Flash chromatography (20% ethyl acetate/hexanes) provided 1.6 g (74%) of a yellow solid.

Sources & evidence

ORD record
ord-c55f7210b2ae4f8999ebbbab1f7c4b92
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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