Dichloromethane → HCID 68639588, compound

HRID 32297Notes

Reaction equation

HRID 32297 reaction equation
CO[CH:3]([C:5]1[C:6]([O:25]CC2C=CC=CC=2)=[CH:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@H:20]([C:21]=2[CH:22]=1)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]1[O:23][CH3:24])[CH3:4].ClCCl>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH2:3]([C:5]1[C:6]([OH:25])=[CH:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@H:20]([C:21]=2[CH:22]=1)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]1[O:23][CH3:24])[CH3:4]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 68621206HCID 68621206, compound

Product 1

HCID 68639588HCID 68639588, compoundYield 104.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

290 mg of 2-(1-methoxyethyl)-3-benzyloxy-17β-methoxy-estra-1,3,5(10)-triene was dissolved in 20 ml each of ethyl acetate and dichloromethane and then mixed with 3 drops of acetic acid and 110 mg of palladium on activated carbon (10%). The hydrogenation was carried out under normal pressure over 8 hours. The catalyst was filtered out, and the solution was concentrated by evaporation in a rotary evaporator and co-evaporated several times with toluene. Flash chromatography (toluene/acetone=80:1) yielded 220 mg (98%) of 2-ethyl-3-hydroxy-17β-methoxy-estra-1,3,5(10)-triene as a colorless foam.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe solution was concentrated by evaporation in a rotary evaporator and co-evaporated several times with toluene

Sources & evidence

ORD record
ord-f707d2acbfe941e4ac674571c4bec624
Source dataset
uspto-grants-2008_09
Patent number
US07427610B2

Reaction notes

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