1,2-Epoxybutane → HCID 12788552, compound

HRID 224249Notes

Reaction equation

HRID 224249 reaction equation
[Cl-].[Cl:2][C:3]1[C:28]([Cl:29])=[C:27]([O:30][CH3:31])[CH:26]=[C:25]([Cl:32])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=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>C1(C)C=CC=CC=1>[Cl:2][C:3]1[C:28]([Cl:29])=[C:27]([O:30][CH3:31])[CH:26]=[C:25]([Cl:32])[C:4]=1/[CH:5]=[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]

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 12651433HCID 12651433, compoundHCID 86735152HCID 86735152, compound

Product 1

HCID 12788552HCID 12788552, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.36 g. (9.54 mmol) of 2,3,6-trichloro-4-methoxybenzyl triphenylphosphonium chloride and 2.0 g. (8.93 mmol) of ethyl (E,Z,E)-4-fluoro-3,7-dimethyl-8-oxo-2,4,6-octatrienoate in 200 ml. of toluene and 150 ml. of 1,2-butylene oxide was heated at 85°-90° C. under argon for 18 hours. The mixture was worked up in the usual manner and the resulting crude product was filtered through 150 g. of silica gel. Elution with methylene chloride gave 2.48 g. of a yellow crystalline substance. Recrystallization of this material from methylene chloride-isopropyl ether yielded 2.21 g. (58% yield) of ethyl (E,Z,E,E)-9-(2,3,6-trichloro-4-methoxyphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate as yellow crystals, mp. 140°-142.5° C.

Workup

  1. additionA mixture of 2.36 g
  2. filtrationthe resulting crude product was filtered through 150 g
  3. washElution with methylene chloride
  4. customgave 2.48 g
  5. customRecrystallization of this material from methylene chloride-isopropyl ether
  6. customyielded 2.21 g

Sources & evidence

ORD record
ord-7fb60423242d4dd49ec9d4abae520e7a
Source dataset
uspto-grants-1980_11
Patent number
US04231944

Reaction notes

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