Dichloromethane → (R)-3-Benzyloxy-1-tert-butyl-dimethylsiloxytetradecane

HRID 233471Notes

Reaction equation

HRID 233471 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC(Cl)(Cl)C(=N)O[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.ClCCl.C(=O)(O)[O-].[Na+]>FC(F)(F)S(O)(=O)=O.C1CCCCC1>[CH2:28]([O:23][C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium BicarbonateHCID 54036929(R)-1-t-Butyldimethylsilyloxy-3-hydroxytetradecane

Product 1

HCID 53803651(R)-3-Benzyloxy-1-tert-butyl-dimethylsiloxytetradecaneYield 88.6%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 8078CyclohexaneSolvent

Procedure

Trifluoromethanesulphonic acid (0.14 mL, 1.6 mmol) was added to a mixture of alcohol 10 (6.9 g, 20 mmol) and benzyl trichloroacetimidate (12.3 g, 49 mmol) in a 1:1 mixture of dichloromethane and cyclohexane (320 mL) at room temperature. After completion of the reaction (5 h) a saturated solution of sodium bicarbonate (50 mL) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 mL) and the organic phases were washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The product was purified by flash chromatography to afford compound 45 as an oil (Rf 0.18, silica, 2% ethyl acetate in hexane, 7.7 g, 88%).

Workup

  1. additionwas added
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  4. washthe organic phases were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-128566932e59459f83118d0fcb2df3bb
Source dataset
uspto-grants-1997_01
Patent number
US05593969

Reaction notes

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