Ozone → 3-(Tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol

HRID 54021Notes

Reaction equation

HRID 54021 reaction equation
O=[O+][O-].[Si:4]([O:21][CH:22]=[C:23]([CH2:27][CH2:28][OH:29])[CH2:24][CH2:25][OH:26])(C(C)(C)C)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[C:23]([C:22](=[C:23]([CH2:27][CH2:28][OH:29])[CH2:24][CH2:25][OH:26])[O:21][SiH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:27])([CH3:24])[CH3:22]

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 187904493-(Tert-butyldiphenylsilyloxymethylene)-1,5-pentanediol

Product 1

HCID 1317195333-(Tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ozone was bubbled through a -78° C. dry methanol (500 mL) solution of 3-(tert-butyldiphenylsilyloxymethylene)-1,5-pentanediol (17 g, 47 mmol) until a blue tint persisted (30 minutes). The reaction was purged with nitrogen (20 min.) and NaBH4 (17.6 g, 47 mmol) was added. The cold bath was removed and the reaction brought to room temperature. The reaction was concentrated in vacuo and the residue partitioned between ether and brine. The ether layer was concentrated and the residue eluted over a silica plug with 0-50% ethyl acetate/hexanes. The minor component was pooled and concentrated to yield the diol, 3-(tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol, 3.8g (22%) of the desired diol as a colorless oil. Overall the yield for the three steps is 17%. MS.

Workup

  1. custom(30 minutes)
  2. additionwas added
  3. customThe cold bath was removed
  4. custombrought to room temperature
  5. concentrationThe reaction was concentrated in vacuo
  6. customthe residue partitioned between ether and brine
  7. concentrationThe ether layer was concentrated
  8. washthe residue eluted over a silica plug with 0-50% ethyl acetate/hexanes
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e64f3bba08114b44829903f32a2d2090
Source dataset
uspto-grants-1997_04
Patent number
US05621098

Reaction notes

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