Ammonia → HCID 22820407, compound

HRID 1156041Notes

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]([OH:21])[C@H:11]([CH3:22])[CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.N.[Li]>C1COCC1.C(O)(C)(C)C>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][C@@H:11]([CH3:22])[C@@H:12]1[OH:21]

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of 10.0 g of 3-methoxy-16α-methyl-1,3,5(10)-estratrien-17β-ol in 200 ml of absolute THF and 20 ml of tert.-butanol is dropped at -50° C. to about 500 ml of ammonia and then combined in incremental portions with 6.3 g of lithium. The mixture is agitated for 3 hours at -40° C., ammonia is allowed to evaporate overnight, the residue is taken up in about 1 liter of water, and extracted with ethyl acetate, thus obtaining 9.6 g of 3-methoxy-16α-methyl-2,5(10)-estradien-17β-ol as an amorphous crude product which is used in the subsequent stage without further purification.

Workup

customto evaporate overnight
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-9ea04bde159549209cb42293987e24d1
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04333928

Reaction notes

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