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

HRID 1940108Notes

Reaction equation

HRID 1940108 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, 3.8 g (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-07cde7e175644fb888110d6c5c82c8da
Source dataset
uspto-grants-1997_12
Patent number
US05698578

Reaction notes

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