Water → HCID 57771498, compound

HRID 2070608Notes

Reaction equation

HRID 2070608 reaction equation
C([Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][C:13]2([CH2:20][CH2:19][CH:18]([O:21][CH3:22])[CH2:17][CH2:16]2)[CH2:12][CH2:11]1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:22][O:21][CH:18]1[CH2:17][CH2:16][C:13]2([CH2:14][CH2:15][CH:10]([CH2:9][OH:8])[CH2:11][CH2:12]2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57771610HCID 57771610, compound

Product 1

HCID 57771498HCID 57771498, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the crude tert-butyl-(9-methoxyspiro[5.5]undec-3-ylmethoxy)-dimethylsilane (393 mg) obtained in Step 5 in tetrahydrofuran (5 mL) was added a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (3 mL) under ice-cooling, followed by stirring the reaction mixture at room temperature for 1.5 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:4) to give (9-methoxyspiro[5.5]undec-3-yl)methanol (217 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:4)

Sources & evidence

ORD record
ord-dd2e8497f2374e598f75b052795c053a
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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