Water → HCID 22261443, compound

HRID 1610254Notes

Reaction equation

HRID 1610254 reaction equation
[OH:1][CH2:2][C:3]1[C:8]2[CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24].O>O1CCCC1>[Si:27]([O:1][CH2:2][C:3]1[C:8]2[CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:7]=2[CH:6]=[CH:5][CH:4]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22261941HCID 22261941, compound

Product 1

HCID 22261443HCID 22261443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(hydroxymethyl)-5,6,7,8,9,10-hexahydrobenzo[a]cycloocten-5-ol (11.51 g, 55.80 mmol), 4-N,N-dimethylaminopyridine (0.5 g) and triethylamine (9.33 ml, 67.0 mmol) in tetrahydrofuran (70 ml) was added tert-butyldimethylchlorosilane (9.25 g, 61.4 mmol) at room temperature and the mixture was stirred as it was overnight at room temperature. The reaction solution was poured into water and extracted twice with ethyl acetate. The collected 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 collected 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-e1d122b7b85143d998347d78cdf0a29c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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