Ethyl Acetate → HCID 66651979, compound

HRID 418966Notes

Reaction equation

HRID 418966 reaction equation
[OH:1][C:2]1[C:3]([C:23](=[O:25])[CH3:24])=[CH:4][C:5]2[CH2:6][CH:7]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH:8]3[CH:13]([C:14]=2[CH:15]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3.[BH4-].[Na+].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[OH:25][CH:23]([C:3]1[C:2]([OH:1])=[CH:15][C:14]2[CH:13]3[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[CH:7]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:6][C:5]=2[CH:4]=1)[CH3:24]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 66652104HCID 66652104, compound

Product 1

HCID 66651979HCID 66651979, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Combine 1-[3-Hydroxy-9-(4-hydroxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl]-ethanone (0.013 g, 0.04 mmol) and NaBH4 (0.016 g, 0.42 mmol) in ethanol (1.5 ml) and heat at 60° C. for 30 minutes. Remove solvent in vacuo and take into ethyl acetate, water, and sodium bicarbonate solution solution. Separate organic layer and wash with water. Dry over anhydrous sodium sulfate and remove solvent in vacuo to yield the titled compound (0.014 g, 100%). 1H NMR (CD30D): 7.16 (d, J=7.9 Hz, 2H), 7.1 (s, 1H), 6.78 (d, J=8.4 Hz, 2H), 5.12 (m, 1H), 3.2 (m, 3H), 2.8 (dd, J=10.5 and 7.5 Hz, 1H), 2.5 (m, 1H), 2.34 (m, 1H), 2.05 (m, 1H), 1.8-1.6 (m, 2H), 1.48 (m, 3H), 1.4-0.8 (m, 4H). MS m/z 337 (M−1).

Workup

  1. washSeparate organic layer and wash with water
  2. dry with materialDry over anhydrous sodium sulfate
  3. customremove solvent in vacuo

Sources & evidence

ORD record
ord-e9bac82f489b4f7f8f6bbca2feb9749e
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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