Water → HCID 178444439, compound

HRID 2227108Notes

Reaction equation

HRID 2227108 reaction equation
[Br-].O1CCCCC1O[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1.C([Li])CCC.[CH2:42]([CH:47]1[CH2:52][CH2:51][CH:50]([CH:53]=O)[CH2:49][CH2:48]1)[CH2:43][CH2:44][CH2:45][CH3:46].[OH2:55]>COC(C)(C)C>[CH2:42]([C@H:47]1[CH2:48][CH2:49][C@H:50]([CH:53]=[CH:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][CH:9]=[CH:14][C:13]=2[OH:55])[CH2:51][CH2:52]1)[CH2:43][CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 962WaterHCID 140856594-PentylcyclohexanalHCID 18471791[3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 178444439HCID 178444439, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a solution of [3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromide 3D (R=pentyl) (1.68 g) in tert-butyl methyl ether at room temperature is added, dropwise, a 2.6 M solution of butyllithium (1.25 mL). The orange reaction mixture is stirred for 30 minutes, then a solution of cyclohexanal 3F (R=pentyl) (0.558 g) in tert-butyl methyl ether (3 mL) is added dropwise. The reaction is stirred a further 30 minutes, then poured into water and extracted with ether. The combined organic layers are washed with brine, then dried over sodium sulfate. The solvent is removed in vacuo and the residual material is flash chromatographed using 10% ethyl acetate in hexanes as the eluent.

Workup

  1. stirringThe reaction is stirred a further 30 minutes
  2. extractionextracted with ether
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customchromatographed

Sources & evidence

ORD record
ord-d061030504034931b997d04d806f93a4
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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