Potassium Carbonate → HCID 86760619, compound

HRID 2057331Notes

Reaction equation

HRID 2057331 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH:18]=O)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(CC)C>[CH2:1]([O:8][C:9](=[O:20])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2733851(4-Bromobutyl)triphenylphosphanium bromideHCID 178485996HCID 178485996, compound

Product 1

HCID 86760619HCID 86760619, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A solution of 126.5 g (459.4 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.27 l 2-methyl-2-butanol was treated with 263.6 g (551.3 mmol) (4-bromobutyl)triphenylphosphonium bromide and 254 g (1838 mmol) of K2CO3 and was heated at reflux for 3.5 h. The reaction was cooled (RT), filtered and evaporated. The residue was suspended in hexane (1.8 l, first at RT then at 0° C.) and filtered. Purification by column chromatography on silica gel (hexane/EtOAc 4:1) gave 149.9 g (83%) of trans-(1 E/Z)-[4-(5-Bromo-pent-1-enyl)-cyclohexyl]-methyl-carbamic acid benzyl ester, MS: 293 (M, 1Br).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfirst at RT then at 0° C.) and filtered
  6. customPurification by column chromatography on silica gel (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-4005ec2e19c74c5c82a97a7853be0a42
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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