2-Butene-1,4-diol → 4-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-ol

HRID 16215

Reaction equation

HRID 16215 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH:4]=[CH:5][CH2:6][OH:7].[C:9]([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])[CH3:10]>O1CCCC1>[C:9]([Si:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[O:7][CH2:6][CH:5]=[CH:4][CH2:3][OH:8])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 80652-Butene-1,4-diolHCID 24758Sodium hydrideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 666569494-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (3 g, 75 mmol, 60% in oil) was added portion-wise to a stirred and cooled (0° C.) solution of but-2-ene-1,4-diol (6 g, 68.09 mmol) in dry tetrahydrofuran (250 mL). After the addition, the mixture was allowed to warm to room temperature and stirred for another two hours. The resulting white mixture was then cooled (0° C.) and tert-butyl-chlorodiphenylsilane (15.7 mL, 61.28 mmol) was added drop wise. After twenty minutes, the cooling bath was removed and the mixture was allowed to stir overnight at room temperature. Saturated NH4Cl was poured into the reaction mixture and the reaction was partitioned with diethyl ether (200 mL). The organic layer was washed with brine, dried (MgSO4), and filtered. The resulting oil was used in the following step without further purification.

Workup

  1. additionAfter the addition
  2. stirringstirred for another two hours
  3. additionwas added drop wise
  4. waitAfter twenty minutes
  5. customthe cooling bath was removed
  6. stirringto stir overnight at room temperature
  7. additionSaturated NH4Cl was poured into the reaction mixture
  8. customthe reaction was partitioned with diethyl ether (200 mL)
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customThe resulting oil was used in the following step without further purification

Sources & evidence

ORD record
ord-cacae96a195b4eb7a82169604af3d677
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Linked notes

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