(2R)-Methyl 5-methoxytetrahydrofuran-2-carboxylate → (2R)-Methyl 5-hydroxytetrahydrofuran-2-carboxylate

HRID 2257227Notes

Reaction equation

HRID 2257227 reaction equation
C[O:2][CH:3]1[O:7][C@@H:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4]1>CO>[OH:2][CH:3]1[O:7][C@@H:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 45089865(2R)-Methyl 5-methoxytetrahydrofuran-2-carboxylate

Product 1

HCID 45090054(2R)-Methyl 5-hydroxytetrahydrofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (2R)-Tetrahydro-5-hydroxy-2-furoate was prepared as for the S-isomer from methyl (2R)-tetrahydro-5-methoxy-2-furoate in similar yield: [α]D25 -9.2° (c=1.8, CH3OH); IR (neat, cm-1) 3543 (br), 2956, 1741, 1068, 1010; 1H NMR (CDCL3) for diastereomer A (58%) δ 5.62 (m, 1H), 4.67 (dd, J=6.5, 8.1 Hz, 1H), 3.78 (s, 3H), 2.46-1.93 (m, 4H); for diastereomer B (42%) δ 5.75 (m, 1H), 4.73 (dd, J=3.8, 8.5 Hz, 1H), 3.76 (s, 3H), 2.46-1.93 (m, 4H); HRMS calculated for C6H10O4 (M+), 146.0579, found 146.0577.

Sources & evidence

ORD record
ord-9442d32530e647e0856886fda24425e9
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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