Diethyl Ether → HCID 178444494, compound

HRID 484284Notes

Reaction equation

HRID 484284 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH2:22][CH:23]=O)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:25](OCC)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:20]([C@H:17]1[CH2:18][CH2:19][C@H:14]([C@H:11]2[CH2:12][CH2:13][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH:23]=[CH2:25]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 178520618HCID 178520618, compound

Product 1

HCID 178444494HCID 178444494, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

A suspension of 5.19 g of methyl-triphenylphosphonium bromide in 80 ml of diethyl ether was treated with 1.55 g of potassium tert.butylate while gassing with nitrogen. The yellow suspension was stirred at room temperature for a further 45 minutes and then treated dropwise at 0° C. with a solution of 2.3 g of 4-[trans-4-[trans-4-(4-fluorophenyl)cyclohexyl]cyclohexyl]butyraldehyde. The reaction mixture was stirred at 0° C. for a further 2 hours and then diluted with 60 ml of water. The aqueous phase was separated and extracted twice with 60 ml of hexane each time. The combined organic phases were washed neutral with water, dried over sodium sulfate, filtered and concentrated. Chromatographic purification of the residue on silica gel with hexane gave 1.89 g of crude product. After two-fold recrystallization from acetone at -20° C. there were obtained 1.22 g of 1-[trans-4-[trans-4-(4-pentenyl)-cyclohexyl]cyclohexyl]-4-fluorobenzene with m.p. (C-N) 65.7° C. and cl.p. (N-I) 129.7° C.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for a further 2 hours
  2. customThe aqueous phase was separated
  3. extractionextracted twice with 60 ml of hexane each time
  4. washThe combined organic phases were washed neutral with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatographic purification of the residue on silica gel with hexane
  9. customgave 1.89 g of crude product
  10. customAfter two-fold recrystallization from acetone at -20° C.

Sources & evidence

ORD record
ord-d505846207b74a7185f709b88bb10d7d
Source dataset
uspto-grants-1993_07
Patent number
US05230826

Reaction notes

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