Tetrahydrofuran → HCID 17946008, compound

HRID 585645Notes

Reaction equation

HRID 585645 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Si:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:18]=[CH:17][C:16]=1C1CCC(=O)CC1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Cl-].[NH4+].[CH2:38]1[CH2:42]OC[CH2:39]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([Si:22]([O:21][C:19]1[CH:18]=[CH:17][C:16]([CH:38]2[CH2:42][CH2:3][C:2](=[CH2:5])[CH2:1][CH2:39]2)=[C:15]([O:14][Si:7]([C:10]([CH3:11])([CH3:13])[CH3:12])([CH3:9])[CH3:8])[CH:20]=1)([CH3:24])[CH3:23])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 17946008HCID 17946008, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (329 mg) in anhydrous THF (10 ml) at 0° C. was added potassium tert-butoxide (103 mg) in one portion. After stirring for 30 min, a solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanone (200 mg) in THF (5 ml) was added. The reaction mixture was stirred for a further 30 min at 0° C., and saturated aqueous ammonium chloride solution (20 ml) was added. The layers were separated and the aqueous layer extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with brine (20 ml), dried over anhydrous magnesium sulphate, and concentrated in vacuo. Purification via flash column chromatography (SiO2 eluting with diethyl ether:petroleum ether, 1:4 v/v) furnished the title compound as a colourless oil (135 mg, 68%). δH (CDCl3): 0.19 (6H, s), 0.24 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.41 (2H, dq), 1.84-1.93 (2H, m), 2.16 (2H, dt), 2.33-2.42 (2H, m), 3.01 (1H, tt), 4.66 (2H, s), 6.29 (1H, dd), 6.40 (1H, dd), 6.94 (1H, d).

Workup

  1. stirringThe reaction mixture was stirred for a further 30 min at 0° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phases were washed with brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customPurification via flash column chromatography (SiO2 eluting with diethyl ether:petroleum ether, 1:4 v/v)

Sources & evidence

ORD record
ord-fbb94498931b4bd2b4abdbac99b87b47
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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