Methanol → 1-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane

HRID 54023Notes

Reaction equation

HRID 54023 reaction equation
[O:1]=[O+][O-].[CH2:4]([O:7][CH2:8][CH:9]([CH2:29][CH:30]=C)[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C=C.N#N.[BH4-].[Na+].[CH3:36][OH:37]>C(OCC)(=O)C.CCCCCC>[OH:37][CH2:36][CH2:4][O:7][CH2:8][CH:9]([CH2:29][CH2:30][OH:1])[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:26])[CH3:27])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 947NitrogenHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 187904481-(2-Propene-1-oxy)-2-(2-propene-1-yl)-3-(tert-butyldiphenylsilyloxy)-propane

Product 1

HCID 187904721-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propaneYield 72%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ozone was bubbled through a -78 ° C. methanol (500 mL) solution of diene, 1-(2-propene-1-oxy)-2-(2-propene-1-yl)-3-(tert-butyldiphenylsilyloxy)-propane, (7.41 g, 18.80 mmol). After the disappearance of the starting material (TLC, 25% ethyl acetate/hexane), the reaction mixture was purged with N2 and sodium borohydride (2.13 g, 56.30 mmol) was added. The reaction was warmed to room temperature. After 12 hours, the reaction was concentrated. The white residue was quenched with water, and extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with brine, dried, and concentrated under reduced pressure to give a residue. The residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent gave the 1,7-diol, 1-(2-hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane (5.48 g, 72% yield). Rf =0.21 (50% ethyl acetate in hexane). NMR.

Workup

  1. additionwas added
  2. concentrationthe reaction was concentrated
  3. customThe white residue was quenched with water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. washThe combined organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. washThe residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent

Sources & evidence

ORD record
ord-739b680f64c048dba1de698e2d6ab1e5
Source dataset
uspto-grants-1997_04
Patent number
US05621098

Reaction notes

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