Triethylamine → HCID 67035742, compound

HRID 2208150Notes

Reaction equation

HRID 2208150 reaction equation
FC(F)(F)S(O[Si:7]([CH3:10])([CH3:9])[CH3:8])(=O)=O.[Si:13]([O:30][CH:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[C:26]([Si:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[O:30][CH:31]1[CH2:36][CH2:35][C:34]([O:37][Si:7]([CH3:10])([CH3:9])[CH3:8])=[CH:33][CH2:32]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 114168864-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexan-1-one

Product 1

HCID 67035742HCID 67035742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trimethylsilyl trifluoromethanesulfonate (45.0 g; 198.8 mmol) is dropped into a solution of known 4{[tert-butyl(diphenyl)silyl]oxy}cyclohexanone [Okamura, W. H.; Elnagar, H. Y.; Ruther, M.; Dobreff, S. J. Org. Chem. 1993, 58, 600] (58.4 g, 165.5 mmol) and triethylamine (55.4 mL; 397.6 mmol) in dichloromethane (500 mL) at −78° C. under an atmosphere of nitrogen. After one hour the reaction mixture is allowed to warm to 0° C. and quenched with saturated NaHCO3-solution (120 mL). The organic layer is separated, dried over MgSO4 and concentrated under reduced pressure. A 1:1-mixture of tert-BuOMe and hexane is added to the biphasic residue. The organic layer is separated, washed with saturated NaHCO3-solution and dried over MgSO4. The solvent is removed under reduced pressure to deliver 69.0 g of the title compound as colourless oil.

Workup

  1. customquenched with saturated NaHCO3-solution (120 mL)
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. additionA 1:1-mixture of tert-BuOMe and hexane is added to the biphasic residue
  6. customThe organic layer is separated
  7. washwashed with saturated NaHCO3-solution
  8. dry with materialdried over MgSO4
  9. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-87dc9e7041f640588b253e73be29654c
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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