4-Pentylcyclohexanal → 2-Benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthalene

HRID 48105Notes

Reaction equation

HRID 48105 reaction equation
[Br-].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:14]=[CH:13]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:40]([CH:45]1[CH2:50][CH2:49][CH:48]([CH:51]=O)[CH2:47][CH2:46]1)[CH2:41][CH2:42][CH2:43][CH3:44].CC(C)([O-])C.[K+]>COC(C)(C)C>[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:20]=[CH:51][CH:48]3[CH2:47][CH2:46][CH:45]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:50][CH2:49]3)[CH:16]=2)[CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 140856594-PentylcyclohexanalHCID 20632177(6-Benzyloxynaphthalen-2-ylmethyl)-triphenyl-phosphonium BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 698847882-Benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthaleneYield 74%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The solution of (6-benzyloxy-naphthalen-2-ylmethyl)-triphenyl-phosphonium bromide (19) (1 equi.), 4-pentyl-cyclohexanecarboxaldehyde (22), and potassium tert-butoxide (1.3 equi.) in tert-butyl methyl ether (6 mL/mmole) was stirred at room temperature for 24 h, then quenched with water, extracted with diethyl ether, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (1.25% EtOAc/hexane) afforded 2-benzyloxy-6-[2-(4-pentyl-cyclohexyl)-vinyl]-naphthalene (23) as a white solid (74%).

Workup

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (1.25% EtOAc/hexane)

Sources & evidence

ORD record
ord-f6c63d21095849468799f3cf0417b9fa
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Reaction notes

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