Me-bpe, (R,R)- → Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

HRID 416190Notes

Reaction equation

HRID 416190 reaction equation
C[C@H]1P(CCP2[C@H](C)CC[C@H]2C)[C@H](C)CC1.[CH3:17][O:18][C:19](=[O:31])[CH2:20][C:21]1[C:25]2[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=2[O:23][CH:22]=1.[H][H]>CO>[CH3:17][O:18][C:19](=[O:31])[CH2:20][CH:21]1[C:25]2[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

5

Reactant 3

HCID 2734555Me-bpe, (R,R)-HCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 57345855Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateYield 41.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (12 mg) and (R,R)-Me-BPE (6.5 mg) was added methanol (2.5 mL) sufficiently substituted with argon gas, and the mixture was stirred at room temperature for 15 min. This was added to methyl(6-hydroxy-1-benzofuran-3-yl)acetate (51 mg), and the mixture was stirred at 70° C. for 3 hr under 0.7 MPa hydrogen atmosphere. The reaction mixture was quantified by HPLC. As a result, the enantiomeric excess was 47.9%, and the yield was 41.5%.

Sources & evidence

ORD record
ord-0dd16be3a2c94008a16169d3569f5fab
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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