HCID 21185922, compound → HCID 21185885, compound

HRID 1384169Notes

Reaction equation

HRID 1384169 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:32])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]([C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])=O)[CH:11]=[CH:10][C:9]1=2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:7][C:8]1([CH3:32])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]([C:22]3[CH:23]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[CH:29]=[CH:30][CH:31]=3)=[CH2:1])[CH:11]=[CH:10][C:9]1=2

Participants

4

Reactant 2

HCID 21185922HCID 21185922, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21185885HCID 21185885, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Potassium tert-butoxide (3 g, 26.5 mmol) is added to a solution of methyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylcarbonyl)benzoate (6.6 g, 18.9 mmol) and methyltriphenylphosphonium bromide (9.4 g, 26.3 mmol) in THP (60 ml). The mixture is stirred for 1 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-8643735ac4c543029ee867f421d11fec
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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