Water → HCID 22262278, compound

HRID 1610659Notes

Reaction equation

HRID 1610659 reaction equation
[OH:1][CH2:2][C:3]1[C:8]2[CH:9]([OH:16])[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].O>O1CCCC1>[Si:28]([O:1][CH2:2][C:3]1[C:8]2[CH:9]([OH:16])[CH2:10][CH2:11][C:12]([CH3:14])([CH3:15])[CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22262081HCID 22262081, compound

Product 1

HCID 22262278HCID 22262278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(hydroxymethyl)-8,8-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (18.87 g, 85.65 mmol), 4-N,N-dimethylaminopyridine (0.5 g) and triethylamine (14.3 ml, 103 mmol) in tetrahydrofuran (100 ml) was added tert-butyldimethylchlorosilane (14.2 g, 94.2 mmol) at room temperature, and the mixture was stirred as it was overnight. The reaction solution was poured into water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1) to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-4814fdefc6cd45f4b5baf97df780ca99
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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