1,4-Butanediol → 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

HRID 1045275Notes

Reaction equation

HRID 1045275 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH3:9][C:10]([Si:13](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:12])[CH3:11]>O>[Si:13]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([C:10]([CH3:12])([CH3:11])[CH3:9])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1,4-butanediol was added sodium hydride (1.0 g of a 60% dispersion in mineral oil). This mixture was allowed to stir at an ambient temperature for 1 h, before TBDPSCl (5.0 mL, 18.2 mmol) was added. The mixture was stirred overnight at an ambient temperature. The reaction mixture was poured into water and extracted with ether (3×100 mL). The combined extract was washed with water and brine and dried over sodium sulfate. Filtration and concentration gave an oily residue, which was purified via radial chromatography on a 4 mm plate eluting with 25% ethyl acetate in hexanes, followed by 50% ethyl acetate in hexane. This gave 3.36 g (56%) of desired product as clear oil. 1H NMR (CDCl3); δ1.24 (s, 9H), 1.65 (m, 4 h), 3.65 (m, 4H), 7.40 (m, 6H), 7.64 (d, 2H, J=1.5 Hz).

Workup

  1. additionwas added
  2. extractionextracted with ether (3×100 mL)
  3. extractionThe combined extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration
  7. customgave an oily residue, which
  8. customwas purified via radial chromatography on a 4 mm plate
  9. washeluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a905b8b12adf4a96b5ca19d5c2b43efe
Source dataset
uspto-grants-2013_10
Patent number
US08568728B2

Reaction notes

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