HCID 15428933, compound → HCID 21185971, compound

HRID 1384164Notes

Reaction equation

HRID 1384164 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I:7][C:8]1[CH:9]=[C:10]([C:14]([C:16]2[C:25]([CH3:26])=[CH:24][C:23]3[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=3[CH:17]=2)=O)[CH:11]=[CH:12][CH:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[I:7][C:8]1[CH:9]=[C:10]([C:14]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][C:25]=2[CH3:26])[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]3([CH3:30])[CH3:29])=[CH2:1])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 15428933HCID 15428933, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21185971HCID 21185971, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (7.26 g, 64.8 [lacuna]) is added to a solution of 3-iodophenyl-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-methanone (20 g, 46.3 mmol) and methyltriphenylphosphonium bromide (21.5 g, 60.2 mmol) in THF (100 ml). The mixture is stirred for 20 h at room temperature. The solution is extracted with ethyl acetate. After separation of the phases by settling, the organic phase is washed twice with 40 ml of water, dried over anhydrous magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica.

Workup

  1. extractionThe solution is extracted with ethyl acetate
  2. customAfter separation of the phases
  3. washthe organic phase is washed twice with 40 ml of water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  6. customThe product is purified by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-2f2e165ce6084514aa39f52c2fa4ce84
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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