Sodium borohydride → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol

HRID 332647

Reaction equation

HRID 332647 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])[CH:18]=[CH:19][CH:20]=1.[BH4-].[Na+]>C(O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[OH:22])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71093140(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanone

Product 1

HCID 71093342(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanolYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanone (4.73 g, 12.35 mmol) in ethanol (100 mL) at 0° C., sodium borohydride (1.88 g, 49.42 mmol) was added portion wise. The coolant was removed, and the reaction mixture was allowed to warm to RT and stirred for 1 hour. The reaction mixture was quenched with water (30 mL) at 0° C. and then concentrated under reduced pressure. The crude material was dissolved in DCM and washed with saturated aqueous ammonium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford the title compound (4.33 g, 91%).

Workup

  1. customThe coolant was removed
  2. customThe reaction mixture was quenched with water (30 mL) at 0° C.
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude material was dissolved in DCM
  5. washwashed with saturated aqueous ammonium chloride
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ee13ebb2715459b98856abc925a9371
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Linked notes

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