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

HRID 2380403Notes

Reaction equation

HRID 2380403 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 persistent 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 persistent 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-31f6df85fcd64bb09f97298cc93627c6
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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