Acetic Acid → HCID 56631149, compound

HRID 1701487Notes

Reaction equation

HRID 1701487 reaction equation
[OH:1][C@@H:2]1[C@@:28]2([CH3:29])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:23])[CH2:15][O:16]C2CCCCO2)[CH2:5][C@@H:4]([OH:31])[CH2:3]1.C(O)(=O)C>O>[CH3:23][C@@H:14]([C@@H:13]1[C@:24]2([CH3:30])[C@H:10]([C@H:9]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:29])[C:6]([CH2:5][C@@H:4]([OH:31])[CH2:3][C@@H:2]2[OH:1])=[CH:7][CH2:8]3)[CH2:11][CH2:12]1)[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13044106HCID 13044106, compound

Product 1

HCID 56631149HCID 56631149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 0.69 g. of (20S)-1α,3β-dihydroxy-20-methyl-21-tetrahydropyranyloxypregna-5-ene in 6.9 ml. of acetic acid and 2.1 ml. of water was warmed to 80° and an additional 3.2 ml. of water was added. The mixture was kept at 80° for one hour, cooled and poured into water. The suspension was extracted with ethyl acetate and the organic solution was washed with saturated sodium bicarbonate solution and water. After drying and evaporation under vacuum, 0.6 g. of (20S)-20-methyl-1α,3β,21-trihydroxypregna-5-ene was obtained. Recrystallization from acetone gave 0.3 g. of colorless prisms, m.p. 208°-209°; [α]D =-29° (c=0.5, methanol).

Workup

  1. temperaturecooled
  2. extractionThe suspension was extracted with ethyl acetate
  3. washthe organic solution was washed with saturated sodium bicarbonate solution and water
  4. customAfter drying
  5. customevaporation under vacuum, 0.6 g

Sources & evidence

ORD record
ord-439fa4edda80420aa3ec71d3318b7c5d
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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