Water → 2-(7-Hydroxymethyl-benzo[b]thiophen-3-yl)-ethanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][C:13]1[C:14]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](OC)=[O:23])[C:15]=2[S:16][CH:17]=1)=O)C.C(OCC)(=O)C.O>C1COCC1>[OH:23][CH2:22][C:18]1[C:15]2[S:16][CH:17]=[C:13]([CH2:12][CH2:10][OH:9])[C:14]=2[CH:21]=[CH:20][CH:19]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen stream, to a solution (38 mL) of lithium aluminum hydride (0.74 g, 19.5 mmol) in THF was added a solution (30 mL) of methyl 3-ethoxycarbonylmethyl-benzo[b]thiophene-7-carboxylate (2.7 g, 9.7 mmol) in THF at 0° C., and the resultant solution was stirred for 10 minutes at the same temperature. To the solution was further added lithium aluminum hydride (0.74 g, 19.5 mmol) at 0° C., and the resultant solution was stirred for 10 minutes at the same temperature. Ethyl acetate was added to the solution, and then water (5.2 mL) was added thereto at 0° C. The temperature of the resultant solution was raised to room temperature, and then the solution was stirred for 10 minutes. The reaction mixture was filtered through Celite. Solvent was then removed by distillation under reduced pressure. The resulting residue was treated by addition of ethyl acetate and n-hexane (1:2), to thereby obtain the titled compound (1.97 g, 98%).
Workup
- customat 0° C.
- customat 0° C
- filtrationThe reaction mixture was filtered through Celite
- customSolvent was then removed by distillation under reduced pressure
- additionThe resulting residue was treated by addition of ethyl acetate and n-hexane (1:2)
Sources & evidence
- ORD record
- ord-f07c633e182849bfb4fc1bd4762ba121
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207134B2
Reaction notes
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