Water → 2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

HRID 627180Notes

Reaction equation

HRID 627180 reaction equation
[H-].[Na+].[CH2:3]=[C:4]([CH2:7][OH:8])[CH2:5][OH:6].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].O>C1COCC1>[Si:9]([O:6][CH2:5][C:4](=[CH2:3])[CH2:7][OH:8])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 770481,3-Propanediol, 2-methylene-

Product 1

HCID 112064702-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a dry flask containing sodium hydride (2.270 g, 56.75 mmol) in THF (150 mL) under N2 at 0° C. was added slowly 2-methylenepropane-1,3-diol (5 g, 56.75 mmol). The reaction was warmed to room temperature and stirred 45 min. TBS-Cl (8.55 g, 56.75 mmol) was added in one batch and stirring was continued for another 45 min, until complete by TLC. To the reaction was added water and the mixture was extracted three times with EtOAc and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated at −10-15° C. Silica gel chromatography (20%-50% EtOAc/Hex) afforded the title compound (11.36 g, 99%) as a clear oil.

Workup

  1. stirringstirring
  2. waitwas continued for another 45 min
  3. extractionthe mixture was extracted three times with EtOAc
  4. washwashed with brine
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated at −10-15° C

Sources & evidence

ORD record
ord-0a9c32aefd22463e89722ae99f2f251b
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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