HCID 12932122, compound → HCID 15120703, compound

HRID 376861Notes

Reaction equation

HRID 376861 reaction equation
[CH2:1]=[C:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[C:15]([OH:18])(=[S:17])[CH3:16]>>[C:15]([S:17][CH2:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4])(=[O:18])[CH3:16]

Participants

3

Reactant 2

HCID 12932122HCID 12932122, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 15120703HCID 15120703, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

3-Phenylpropylialonic acid (6.14 g) was converted to 2-methylene-5-phenylpentanoic acid (2.1 g, 40%) by the method described in Example 32a). δH (CDCl3) 1.88 (2 H, m, CH2), 2.37 (2 H, t, J 7.6 Hz, CH2), 2.67 (2 H, t, J 7.6 Hz, CH2), 5.68 and 6.33 (2 H, 2×s, ##STR9## 7.26 (5 H, m, Ph). The solid was dissolved in thioacetic acid (5 ml) and heated at 100° C. for 2 hours. Evaporated to give the title compound (2.9 g, 100%); δH (CDCl3) 1.71 (4 H, m, 2×CH2), 2.33 (3 H, s, COCH3), 2.64 (3 H, m, CH, CH2), 3.08 (2 H, m, CH2), 7.27 (5 H, m, Ph).

Workup

  1. customEvaporated

Sources & evidence

ORD record
ord-609829ef1d874bb5b074334c28237371
Source dataset
uspto-grants-2000_02
Patent number
US06022885

Reaction notes

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