tert-Butyl methyl ether → HCID 178447843, compound

HRID 486354Notes

Reaction equation

HRID 486354 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].CO[C:25](C)(C)[CH3:26]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[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)=[CH:25][CH3:26]

Participants

4

Reactant 2

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

Product 1

HCID 178447843HCID 178447843, compound

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

A suspension of 5.892 g of ethyltriphenylphosphonium bromide in 75 ml of tert.-butyl methyl ether was treated with 1.801 g of potassium tert.-butylate while stirring and gassing with nitrogen and stirred at room temperature for 1.5 hours. Subsequently, the suspension was treated dropwise at 2° C. within 45 minutes with a solution of 2.269 g of trans-4-(3',4'-difluoro-4-biphenylyl)cyclohexanecarboxaldehyde (prepared according to Example 3) in 17 ml of tert.-butyl methyl ether, stirred for a further 45 minutes and concentrated in a vacuum. The residue (9.7 g) was taken up in 50 ml of hexane, stirred and filtered. Concentration of the filtrate in a vacuum and chromatographical purification of the crude product obtained on silica gel with methylene chloride gave 2.464 g of 4-[trans-4-(propenyl)cyclohexyl]-3',4'-difluorobiphenyl (89.7% Z; 10.1% E).

Workup

  1. stirringstirred at room temperature for 1.5 hours
  2. stirringstirred for a further 45 minutes
  3. concentrationconcentrated in a vacuum
  4. stirringstirred
  5. filtrationfiltered
  6. customConcentration of the filtrate in a vacuum and chromatographical purification of the crude product
  7. customobtained on silica gel with methylene chloride

Sources & evidence

ORD record
ord-b5879bc5109a4590b154fe13d2989701
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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