Sodium Hydroxide → (4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

HRID 574941Notes

Reaction equation

HRID 574941 reaction equation
[F:1][C:2]1([C:16](OCC)=[O:17])[CH2:7][CH2:6][C:5]2([O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1([CH2:16][OH:17])[CH2:3][CH2:4][C:5]2([O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11]2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67126734Ethyl 4'-fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-carboxylate

Product 1

HCID 67126697(4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 350B (23 g) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (3.11 g). The mixture was stirred overnight. Aqueous 2N NaOH solution was added dropwise to the reaction mixture. The mixture was then diluted with ethyl acetate (600 mL) and washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product which was loaded on a 600 g analogics column and eluted with 10% to 20% ethyl acetate in hexane to provide the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent
  4. customgave the crude product which
  5. washeluted with 10% to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4c25e92015a6458bad8c2c69921b6192
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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