Methanol → 8-(3-Hydroxypropyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1586959Notes

Reaction equation

HRID 1586959 reaction equation
[CH2:1]1[O:15][C:4]2([CH2:9][CH2:8][C:7]([CH2:11][CH2:12][CH:13]=C)([OH:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[BH4-].[Na+].C[OH:19]>>[CH2:1]1[O:15][C:4]2([CH2:9][CH2:8][C:7]([CH2:11][CH2:12][CH2:13][OH:19])([OH:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 542418378-(But-3-en-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 538660308-(3-Hydroxypropyl)-1,4-dioxaspiro[4.5]decan-8-ol

Procedure

A mixture of 4-(3-Butenyl)-4-hydroxy-cyclohexanone ethylene ketal (1.8 g) in methanol (40 mL) was ozonized at -70° C. until a persistant blue color was obtained. The ozonide was decomposed with excess sodium borohydride at -60° C. The reaction was concentrated in vacuo and the residue was partitioned between brine and ethyl acetate. The aqueous layer was extracted several more times with ethyl acetate and the combined organic extracts were dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified by flash chromatography with ethyl acetate as the eluent to afford 4-(3-Hydroxypropyl)-4-hydroxy-cyclohexanone ethylene ketal as an oil.

Workup

  1. customwas ozonized at -70° C. until a persistant blue color
  2. customwas obtained
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe residue was partitioned between brine and ethyl acetate
  5. extractionThe aqueous layer was extracted several more times with ethyl acetate
  6. dry with materialthe combined organic extracts were dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by flash chromatography with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6bed46354cef459b8f3c8fe2fd63c2b5
Source dataset
uspto-grants-1993_06
Patent number
US05216159

Reaction notes

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