HCID 20285742, compound → HCID 131710956, compound

HRID 1764572Notes

Reaction equation

HRID 1764572 reaction equation
[Cl-].[Cl:2][C:3]1[S:7][C:6]([CH3:8])=[C:5]([Cl:9])[C:4]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([C:32]([CH3:44])=[CH:33][CH:34]=[CH:35][C:36]([CH3:43])=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=O>C1OCCC1>[CH2:41]([O:40][C:38](=[O:39])[CH:37]=[C:36]([CH3:43])/[CH:35]=[CH:34]/[CH:33]=[C:32]([CH3:44])[CH:30]=[CH:10][C:4]1[C:5]([Cl:9])=[C:6]([CH3:8])[S:7][C:3]=1[Cl:2])[CH3:42]

Participants

4

Reactant 2

HCID 20285742HCID 20285742, compoundHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate

Product 1

HCID 131710956HCID 131710956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10.83 g. (22.6 mmol) of (2,4-dichloro-5-methyl-3-thenyl)triphenyl phosphonium chloride and 5.15 g. (24.8 mmol) of ethyl 7-formyl-3-methyl-2,4,6-octatrienoate in 350 ml. of butylene oxide was heated to 70° C. for 4.5 hrs. The resulting clear solution was cooled, poured into 500 ml. of a methanol/water mixture (6:4) and extracted with hexane. The combined hexane extracts were washed with methanol/water (6:4), dried and evaporated. The resulting crude material was purified by chromatography (silica gel, hexane/ethyl acetate = 4:1) to yield after recrystallization from hexane, all trans-3,7-dimethyl-9-(2,4-dichloro-5-methyl-3-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester, m.p. 99°-100° C.

Workup

  1. additionA suspension of 10.83 g
  2. temperatureThe resulting clear solution was cooled
  3. additionpoured into 500 ml
  4. extractionof a methanol/water mixture (6:4) and extracted with hexane
  5. washThe combined hexane extracts were washed with methanol/water (6:4)
  6. customdried
  7. customevaporated
  8. customThe resulting crude material was purified by chromatography (silica gel, hexane/ethyl acetate = 4:1)
  9. customto yield
  10. customafter recrystallization from hexane, all trans-3,7-dimethyl-9-(2,4-dichloro-5-methyl-3-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester, m.p. 99°-100° C.

Sources & evidence

ORD record
ord-c1f52f13c15d40c589e69455b33eba85
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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