tert-Butyl methyl ether → HCID 178455705, compound

HRID 486355Notes

Reaction equation

HRID 486355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([CH:21]=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:23]OC(C)(C)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:21]([C@H:18]1[CH2:19][CH2:20][C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)=[CH2:23]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 178520915HCID 178520915, compound

Product 1

HCID 178455705HCID 178455705, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A suspension of 0.977 g of methyltriphenylphosphonium bromide in 12 ml of tert.-butyl methyl ether was treated with 0.308 g of potassium tert.-butylate while stirring and gassing with nitrogen and stirred at room temperature for a further 1.5 hours. The yellow suspension was treated dropwise at 2° C. within 15 minutes with a solution of 0.439 g of trans-4-(3',4'-difluoro-4-biphenylyl)cyclohexanecarboxaldehyde in 12 ml of tert.-butyl methyl ether, stirred at room temperature for a further 1.5 hours and concentrated in a vacuum. Purification of the residue by chomatography on silica gel with methylene chloride and subsequent two-fold recrystallization from hexane gave 0.118 g of pure 4-(trans-4-vinylcyclohexyl)-3',4'-difluorobiphenyl; m.p. (C-N) 97.0° C., cl.p. (N-I) 84.7° C.

Workup

  1. stirringstirred at room temperature for a further 1.5 hours
  2. stirringstirred at room temperature for a further 1.5 hours
  3. concentrationconcentrated in a vacuum
  4. customPurification of the residue by chomatography on silica gel
  5. customwith methylene chloride and subsequent two-fold recrystallization from hexane

Sources & evidence

ORD record
ord-72fc01d231384f2297aa76145083ce5a
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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