Isopropanol → (2-Isopropoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester

HRID 900594Notes

Reaction equation

HRID 900594 reaction equation
[CH2:1]([O:4][C:5](=[O:22])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13][CH2:14][CH2:15]C1C=CC=CC=1)[CH:2]=[CH2:3].[CH:23](O)(C)C>>[CH2:1]([O:4][C:5](=[O:22])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13][CH:14]([CH3:15])[CH3:23])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 18465651(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl ester

Product 1

HCID 18465855(2-Isopropoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl esterYield 81%

Procedure

Prepared as described for compound 40 using isopropanol to afford 3.80 grams (81% yield) of the title compound as a colorless oil. 1H-NMR (500 MHz, CDCl3) δ 1.10-1.35 (m, 6H), 2.32-2.60 (m, 1H), 2.82 (dd, 0.5H), 3.02 (dd, 0.5H), 3.82-4.11 (m, 1H), 4.48-4.66 (m, 3H), 5.20-5.36 (m, 2H), 5.54 (dd, 1H), 5.82-6.05 (m, 1H). LC-MS (ES+): m/e=244.2 (M+H+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f435a8b847014d28aed362c7efb6841f
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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