HCID 86658513, compound → HCID 86658512, compound

HRID 2093248Notes

Reaction equation

HRID 2093248 reaction equation
C([S:4][CH:5]([CH3:14])[CH:6]([CH3:13])[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])(=O)C>C(O)(C)C>[SH:4][CH:5]([CH3:14])[CH:6]([CH3:13])[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8]

Participants

3

Reactant 1

HCID 86658513HCID 86658513, compound

Product 1

HCID 86658512HCID 86658512, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Conditions are the same as for Example 2, but with the product of Example 5 as the starting component and isopropyl alcohol as solvent; 37% yield. Odor: at 1 ppm in DPG—exotic fruit, sweet, sulfury, fatty, floral, slightly rosy. GC/MS (EI): m/z (%) 176(48), 143(14), 134(72), 117(51), 89(91), 61(93), 56(100). 1H NMR (CDCl3): δ 4.98-5.05 (m, 1H), 3.14-3.30 (m, 1H), 2.42-2.53 (m, 1H), 1.67 & 1.49 (2d, J=7.33 Hz, 1H mix of diastereomers), 1.31-1.35 (m, 3H), 1.17-1.25 (m, 9H). 13C NMR (CDCl3) for mix of diastereomers: δ 174.2, 68.3, 67.6, 48.8, 47.9, 37.8, 23.6, 21.8, 14.2, 13.5.

Workup

  1. addition13C NMR (CDCl3) for mix of diastereomers

Sources & evidence

ORD record
ord-1f0a0cf1623347ac896bdf6e664d13a6
Source dataset
uspto-grants-2013_05
Patent number
US08445051B2

Reaction notes

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