Water → HCID 86759645, compound

HRID 1815787Notes

Reaction equation

HRID 1815787 reaction equation
[CH3:1][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])[C@H:12]([CH2:21][OH:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.CC(O)C.O>CS(C)=O.C(N(CC)CC)C>[CH3:1][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])[C@H:12]([CH:21]=[O:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 69790361HCID 69790361, compound

Product 1

HCID 86759645HCID 86759645, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8471TriethylamineSolvent

Procedure

i)—A solution of sulfur trioxide pyridine complex (50.0 g) in dimethyl sulfoxide (250 ml) was added in 15 min. to a solution of (14β,17α)-3-methoxyestra-1,3,5(10)-triene-17-methanol (Example 1, step ii; 23.6 g) in a mixture of dimethyl sulfoxide (425 ml) and triethylamine (70 ml). After 20 min. stirring, 2-propanol (88 ml) was added and stirring was continued for 15 min. The reaction mixture was poured into water (1300 ml) and the product was extracted into dichloromethane. The combined organic phases were washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. Trituration (water/ethanol, first 3:2, then 1:1) afforded (14β,17α)-3-methoxyestra-1,3,5(10)-triene-17-carboxaldehyde (18.8 g).

Workup

  1. stirringstirring
  2. waitwas continued for 15 min
  3. extractionthe product was extracted into dichloromethane
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b89cd3d396e7423d8f592d98c9bc29d4
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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