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Tetrahydrofuran → Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane

HRID 2307110
Notes
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Reaction equation

HRID 2307110 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 17946008Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilaneYield 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-ec1f459edae541548b0c3ae7e97c75bd
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06828460B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes