Dichloromethane → 1-(tert-Butyldimethylsilyloxy)-2-propanone

HRID 709904

Reaction equation

HRID 709904 reaction equation
C(Cl)Cl.[OH:4][CH2:5][C:6](=[O:8])[CH3:7].CCN(CC)CC.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C1C=CN=CC=1)C.O>[Si:20]([O:4][CH2:5][C:6](=[O:8])[CH3:7])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8299HydroxyacetoneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanoneYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a DCM (5 mL) solution of 1-hydroxypropan-2-one (500 mg, 6.8 mmol), DMAP (41 mg, 0.34 mmol) and Et3N (1.2 mL, 8.16 mmol) was added TBSCl (1.133 g, 7.5 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. Then the mixture was added water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (10/1) to give the title compound (950 mg, 75%). EDI-MS (M+1): 189. 1H NMR (300 MHz, CDCl3) δ 4.057 (s, 2H), 2.080 (s, 3H), 0.832 (s, 9H), 0.001 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e48db2831a6490e90b4fc5c64604832
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Linked notes

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