Water → HCID 90037844, compound

HRID 1749386Notes

Reaction equation

HRID 1749386 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11](=[O:12])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[BH4-].[Na+].C(OCC)(=O)C.O>CO>[CH3:1][C:2]1([CH3:13])[CH:11]([OH:12])[CH2:10][CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 111713897,7-diMethyl-1,4-dioxaspiro[4.5]decan-8-one

Product 1

HCID 90037844HCID 90037844, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-one (1.0 equiv.) in MeOH (0.5 M) was added sodium borohydride (1.0 equiv.) slowly at 0° C. under nitrogen, and the resulting reaction mixture was stirred at room temperature for 60 min. TLC (petroleum ether:ethyl acetate=10:1) showed that the reaction was completed. Water was added, and the solvent was removed under reduced pressure. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to give 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-ol (99% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.85-3.94 (m, 4H), 3.37-3.40 (m, 1H), 1.41-1.81 (m, 7H), 0.97 (s, 6H).

Workup

  1. customthe resulting reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d290da3efc724a7b8dc027236e0ba76d
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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