Hydrochloric Acid → HCID 57213455, compound

HRID 2215942Notes

Reaction equation

HRID 2215942 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@:13]([CH2:15][CH2:16]3)([CH3:14])[CH2:12][C@H:11]([OH:21])[CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)C.Cl>C1(C)C=CC=CC=1>[CH3:14][C@@:13]12[CH2:15][CH2:16][C@H:17]3[C@@H:8]([CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([OH:2])[CH:20]=[CH:19][C:18]=43)[C@@H:9]1[CH2:10][C@@H:11]([OH:21])[CH2:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 21225700DiisobutylaluminumhydrideHCID 54311966HCID 54311966, compound

Product 1

HCID 57213455HCID 57213455, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.55 g of 3-methoxy-13α-estra-1,3,5(10)-trien-16α-ol is dissolved hot under a cover gas in 10 ml of toluene. A mixture of 2.3 ml of diisobutylaluminum hydride and 5.4 ml of toluene is added in drops to this solution and refluxed until the reaction is completed (about 4 hours). 2.1 ml of ethanol is added to the cooled batch, and 6 ml of semi-concentrated hydrochloric acid is carefully added while being cooled. After extraction with ethyl acetate, the organic phase is washed neutral and dried on magnesium sulfate. 362 mg of 13α-estra-1,3,5(10)-triene-3,16α-diol is obtained. The recrystallization from methanol yields colorless crystals; flash point 224 . . . 231° C.; [α]D=+61° (pyridine, c=1.13).

Workup

  1. additionis added in drops to this solution
  2. temperaturerefluxed until the reaction
  3. custom(about 4 hours)
  4. additionis carefully added
  5. temperaturewhile being cooled
  6. extractionAfter extraction with ethyl acetate
  7. washthe organic phase is washed neutral
  8. customdried on magnesium sulfate

Sources & evidence

ORD record
ord-7c237e7d539f45e4b9385005ca2b982b
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

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