(4-Carboxybutyl)triphenylphosphonium bromide → HCID 86747752, compound

HRID 1463936Notes

Reaction equation

HRID 1463936 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].CC(C)([O-])C.[K+].[CH2:34]1[CH2:55][O:54][CH:36]([CH2:37][CH:38]2[CH:45]([O:46][CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)[CH2:44][CH:43]3[CH:39]2[CH2:40][CH:41](O)[O:42]3)[O:35]1>C1COCC1>[CH2:34]1[CH2:55][O:54][CH:36]([CH2:37][C@H:38]2[C@H:45]([O:46][CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)[CH2:44][C@H:43]([OH:42])[C@@H:39]2[CH2:40]/[CH:41]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[O:35]1

Participants

5

Reactant 3

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 86747751HCID 86747751, compound

Product 1

HCID 86747752HCID 86747752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Carboxybutyl)triphenylphosphonium bromide (22.03 g) and potassium t-butoxide (1-M, 99.4 ml) were treated in THF (100 ml) to give a ylide, to which was added the previously obtained lactol (58) at 0° C., and the mixture was kept at room temperature overnight. The reaction was worked up in the usual manner to give the carboxylic acid

Workup

  1. customto give a ylide

Sources & evidence

ORD record
ord-ba122d84737e46a88fa9828a039173e5
Source dataset
uspto-grants-1994_04
Patent number
US05302617

Reaction notes

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