Water → HCID 86691335, compound

HRID 881998Notes

Reaction equation

HRID 881998 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:7]([CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH2:8])[CH2:5][OH:6].C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:6][CH2:5][CH:4]([C:7]([CH2:9][Si:10]([CH3:13])([CH3:11])[CH3:12])=[CH2:8])[CH2:3][CH:2]([CH3:14])[CH3:1])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86691336HCID 86691336, compound

Product 1

HCID 86691335HCID 86691335, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentan-1-ol (59.1 mg, 0.275 mmol) and triethyl amine (835 mg, 8.25 mmol) were dissolved in anhydrous CH2Cl2 (20 mL), and then the solution was cooled to 0° C. p-toluenesulfonyl chloride (57.7 mg, 0.303 mmol) and DMAP (2.00 mg, 0.0138 mmol) were added thereto and the resulting solution was stirred at 0° C. for 6 hr. Water (30 mL) was added thereto to complete the reaction, extraction was performed by using CH2Cl2 (3×20 mL), an organic layer was washed with a brine solution, anhydrous magnesium sulfate was used to perform drying and distillation under reduced pressure, and then column chromatography was used to obtain 75.1 mg (yield 74%) of the title compound which is colorless and in the oil state.

Workup

  1. additionwere added
  2. customthe reaction, extraction
  3. washan organic layer was washed with a brine solution, anhydrous magnesium sulfate
  4. customto perform drying
  5. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-9c1cca87891f45ec8ad5019bee698b17
Source dataset
uspto-grants-2015_03
Patent number
US08993766B2

Reaction notes

Loading…