HuagongsheHuagongshe Chemistry Print Report · For research reference only
(R)-5-(3-methoxyallyl)-2,2-dimethyl-1,3-dioxolan-4-one → (2R)-Methyl 5-methoxytetrahydrofuran-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (R)-5-(3-methoxyallyl)-2,2-dimethyl-1,3-dioxolan-4-one | HCID 54185112 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (2R)-Methyl 5-methoxytetrahydrofuran-2-carboxylate | HCID 45089865 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05504107 |
| Source dataset | uspto-grants-1996_04 |
| ORD ID | ord-8a8e957533ee42dda5f9e6a21d6a3c84 |
| Source note | uspto-grants-1996_04 |