Triethylamine → HCID 11407885, compound

HRID 2304854Notes

Reaction equation

HRID 2304854 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([OH:19])([C:15]([F:18])([F:17])[F:16])/[CH:4]=[CH:5]\[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[O:12].C(N(CC)CC)C.[CH2:29]([Si:31](Cl)([CH2:34][CH3:35])[CH2:32][CH3:33])[CH3:30]>C1COCC1.CN(C)C1C=CN=CC=1>[F:1][C:2]([F:20])([F:21])[C:3]([O:19][Si:31]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:29][CH3:30])([C:15]([F:17])([F:18])[F:16])/[CH:4]=[CH:5]\[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 23245522HCID 23245522, compound

Product 1

HCID 11407885HCID 11407885, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.73 g of (Z)-10,10,10-trifluoro-9-hydroxy-5,5-dimethyl-9-trifluoromethyl-dec-7-enal in 67 ml of THF was added at 22° subsequently 2.55 g of triethylamine, 0.128 g of 4-dimethylamino pyridine and 3.92 g of triethylsilyl chloride and the solution was stirred at 22° for 1.5 h after which time g.l.c. indicated completion of the reaction. The suspension was evaporated, the residue dissolved in dichloromethane and washed with 0.1 N of aqueous hydrochloric acid and with sat. aqueous NaCl. The organic layer was dried over MgSO4, evaporated and the residue was chromatographed over silica with hexane/AcOEt 15:1 to give 7.50 g of the pure (99%, g.l.c.) title compound as a colorless liquid. IR (neat): 1729s (C═O), 1661w (C═C). MS (EI): 405/10 M−C2H5).

Workup

  1. customcompletion of the reaction
  2. customThe suspension was evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with 0.1 N of aqueous hydrochloric acid and with sat. aqueous NaCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customthe residue was chromatographed over silica with hexane/AcOEt 15:1

Sources & evidence

ORD record
ord-97156e0e1fbb498aab39e94b515151ea
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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