1,2-Epoxybutane → HCID 12651443, compound

HRID 1075334Notes

Reaction equation

HRID 1075334 reaction equation
[Cl-].[Cl:2][C:3]1[C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:7]([CH3:29])[C:6]([CH3:30])=[C:5]([O:31][CH3:32])[CH:4]=1.[F:33]/[C:34](=[CH:43]\[CH:44]=[C:45](/[CH3:48])\[CH:46]=O)/[C:35](/[CH3:42])=[CH:36]/[C:37]([O:39][CH2:40][CH3:41])=[O:38].C1OC1CC>CCOCC>[Cl:2][C:3]1[C:8](/[CH:9]=[CH:48]/[C:45](/[CH3:46])=[CH:44]/[CH:43]=[C:34](\[F:33])/[C:35](/[CH3:42])=[CH:36]/[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:7]([CH3:29])[C:6]([CH3:30])=[C:5]([O:31][CH3:32])[CH:4]=1

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 12651433HCID 12651433, compoundHCID 86736594HCID 86736594, compound

Product 1

HCID 12651443HCID 12651443, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6.0 g. (12.46 mmol) of 6-chloro-4-methoxy-2,3-dimethylbenzyl triphenylphosphonium chloride and 2.71 g. of ethyl (E,Z,E)-4-fluoro-3,7-dimethyl-8-oxo-2,4,6-octatrienoate in 15 ml. of 1,2-butylene oxide was heated at 110° C. in a sealed tube for 60 hours. The resulting mixture was worked up with ether in the usual manner to give 13.53 g. of crude product. This material was chromatographed on 300 g. of silica gel. Elution with 1:4 ether-petroleum ether yielded 4.65 g. of yellow crystals. Recrystallization of this material from methylene chloride-petroleum ether afforded 1.67 g. (35% yield) of pure ethyl (E,Z,E,E)-9-(6-chloro-4-methoxy-2,3-dimethylphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate as yellow crystals, mp. 126°-128° C.

Workup

  1. additionA mixture of 6.0 g
  2. customto give 13.53 g
  3. customThis material was chromatographed on 300 g
  4. washElution with 1:4 ether-petroleum ether
  5. customyielded 4.65 g
  6. customRecrystallization of this material from methylene chloride-petroleum ether
  7. customafforded 1.67 g

Sources & evidence

ORD record
ord-6e840da1283140e1bdf66f05b9ebc2ad
Source dataset
uspto-grants-1983_07
Patent number
US04395575

Reaction notes

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