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

HRID 1908920Notes

Reaction equation

HRID 1908920 reaction equation
C[C@H]1P(CCP2[C@H](C)CC[C@H]2C)[C@H](C)CC1.[CH3:17][O:18][C:19]1[CH:32]=[CH:31][C:22]2[C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][O:25][C:21]=2[CH:20]=1.[H][H]>CO>[CH3:17][O:18][C:19]1[CH:32]=[CH:31][C:22]2[CH:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:24][O:25][C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 2734555Me-bpe, (R,R)-HCID 15618717Methyl 2-(6-methoxy-1-benzofuran-3-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 59342592Methyl 6-Methoxy-2,3-dihydrobenzofuran-3-acetateYield 24.3%

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 by argon gas, and the mixture was stirred at room temperature for 15 min. This was added to methyl (6-methoxy-1-benzofuran-3-yl)acetate (55 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 52.8%, and the yield was 24.3%.

Sources & evidence

ORD record
ord-aabb859dacfb423f9fd624d1ec3ff196
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

Loading…