Sulfuric Acid → HCID 86735583, compound

HRID 1679767Notes

Reaction equation

HRID 1679767 reaction equation
[C:1]([O:4][C@@:5]1([C:25]#[CH:26])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH2:7][CH3:8])[C@@H:20]1[C:15](=[CH:16][C:17](=[O:24])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2].O1CCCC1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].S(=O)(=O)(O)O>CC(C)=O.CCCCCC>[C:1]([O:4][C@@:5]1([C:25]#[CH:26])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH2:7][CH3:8])[C@@H:20]1[C:15](=[CH:16][C@@H:17]([OH:24])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8028Tetrahydrofuran2×HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86735582Gestodene acetate

Product 1

HCID 86735583HCID 86735583, compound

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

Procedure

Analogously to Example 13, 1.5 g. of 17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one in 40 ml. of tetrahydrofuran is reacted with 4.5 g. of lithium tri-(tert.butoxy)-aluminum hydride in 30 ml. of tetrahydrofuran. After 1 hour, the solution is introduced into ice water which contains sulfuric acid and worked up analogously to Example 13. After chromatography of the crude product on silica gel with 5-8% acetone-hexane, 530 mg. of 17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3β-ol is obtained.

Sources & evidence

ORD record
ord-4e413ed1024c467a9ecb227025750391
Source dataset
uspto-grants-1978_03
Patent number
US04081537

Reaction notes

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