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

HRID 1975496Notes

Reaction equation

HRID 1975496 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-ed80772fb11a4379a437ea121f1e0590
Source dataset
uspto-grants-1994_02
Patent number
US05286860

Reaction notes

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