Acetic Acid → (1S)-1-(1-benzothiophen-3-yl)ethan-1-ol

HRID 1691668Notes

Reaction equation

HRID 1691668 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[O:12])[CH3:11])=[CH:2]1.CC(C)[O-].[Na+].C(O)(=O)C>C(O)(C)C.[Rh]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@@H:10]([OH:12])[CH3:11])=[CH:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 143163-AcetylbenzothiopheneHCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 25128401(1S)-1-(1-benzothiophen-3-yl)ethan-1-olYield 99.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

To a solution of 4.45 g of 1-(1-benzothiene-3-yl)ethanone in 95 mL of isopropanol was added the asymmetric rhodium catalyst solution prepared as described above. Under reduced pressure (about 6600 Pa), an isopropanol solution of sodium isopropoxide (0.1 M, 10.0 mL) was added thereto. Further, the pressure was reduced to about 3700 Pa, followed by stirring at room temperature for 2 hours. To the reaction mixture was added acetic acid (2 mL) to stop the reaction, followed by concentrating under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain (1S)-1-(1-benzothiene-3-yl)ethanol (4.48 g, 94% ee) as a pale yellow oily substance. (HPLC analysis condition: CHIRALCEL OD-H column manufactured by (DAICEL CHEMICAL INDUSTRIES. Ltd., eluting solvent hexane/isopropanol=90/10, flow rate 1.0 mLmin−1, retention time: 8.1 min (S-isomer), 12.6 min (R-isomer)) EI: 178

Workup

  1. customprepared
  2. customthe reaction
  3. concentrationby concentrating under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-93327c6073574491a48036c309f6e91f
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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