(R)-5-(3-methoxyallyl)-2,2-dimethyl-1,3-dioxolan-4-one → (2R)-Methyl 5-methoxytetrahydrofuran-2-carboxylate

HRID 1720078Notes

Reaction equation

HRID 1720078 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][CH2:5][C@H:6]1[O:10][C:9](C)(C)[O:8][C:7]1=[O:13]>CO>[CH3:1][O:2][CH:3]1[O:10][C@@H:6]([C:7]([O:8][CH3:9])=[O:13])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 54185112(R)-5-(3-methoxyallyl)-2,2-dimethyl-1,3-dioxolan-4-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (2R)-Tetrahydro-5-methoxy-2-furoate was prepared as for the S-isomer from (R)-5-(3-methoxyallyl)-2,2-dimethyl-1,3-dioxolane-4-one in similar yield: α!D25 -28.33° (c=0.1, CH3OH); IR (neat, cm-1) 2956, 1754, 1209, 1105; 1H NMR (CDCl3) diastereomer A (66%) δ 5.21 (m, 1H), 4.64-4.52 (m, 1H), 3.77 (s, 3H), 3.38 (s, 3H), 2.42-1.84 (m, 4H) for diastereomer B (33%) 5.08 (m, 1H), 4.64-4.52 (m, 1H), 3.77 (s, 3H), 3.42 (s, 3H), 2.42-1.84 (m, H); HRMS calculated for C7H12O4 (M+) 160.0735, found 160.0750.

Sources & evidence

ORD record
ord-8a8e957533ee42dda5f9e6a21d6a3c84
Source dataset
uspto-grants-1996_04
Patent number
US05504107

Reaction notes

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