Tetrahydrofuran → trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate

HRID 2202261Notes

Reaction equation

HRID 2202261 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:22][C@H:21]1[CH2:23][OH:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C1COCC1>O>[CH3:25][S:26]([O:24][CH2:23][C@@H:21]1[CH2:22][C@H:20]1[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 10042906trans-(2-((Tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol

Product 1

HCID 10025044trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TEA (0.450 mL, 3.23 mmol) was added to a mixture of trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol (1 g, 2.94 mmol), methanesulfonyl chloride (0.250 mL, 3.23 mmol) and THF (10 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give trans-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate (1.230 g, 2.94 mmol, 100%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-205e3c611ce84a34b53fb074622e9c7b
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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