Water → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10),15-tetraen-17-ol

HRID 328212Notes

Reaction equation

HRID 328212 reaction equation
C([Li])(C)(C)C.[O:6]1[C@H:8]2[C@:9]3([CH2:25][CH2:24][C@H:23]4[C@@H:14]([CH2:15][CH2:16][C:17]5[CH:18]=[C:19]([O:26][CH3:27])[CH:20]=[CH:21][C:22]=54)[C@@H:12]3[CH2:13][C@@H:7]12)[CH2:10][CH3:11].O>CCCCC.CCOCC>[CH3:27][O:26][C:19]1[CH:20]=[CH:21][C:22]2[C@@H:23]3[C@H:14]([C@H:12]4[C@@:9]([CH2:25][CH2:24]3)([CH2:10][CH3:11])[C@H:8]([OH:6])[CH:7]=[CH:13]4)[CH2:15][CH2:16][C:17]=2[CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8673462416alpha,17alpha-Epoxy-3-methoxy-18-methyl-1,3,5(10)-estratrieneHCID 178418306HCID 178418306, compound

Product 1

HCID 86734623(17beta)-13-Ethyl-3-methoxygona-1,3,5(10),15-tetraen-17-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Procedure

At 0° C. and under argon, 4 ml. of a 2-molar tert.-butyllithium solution in pentane is added to 450 mg. of 16α,17α-epoxy-3-methoxy-18-methyl-1,3,5(10)-estratriene in 12 ml. of ether. After 1 hour, the solution is diluted with ether, gently mixed with water, washed neutral, and dried over sodium sulfate. After purifying the crude product by preparative layer chromatography (system: hexane/ethyl acetate = 7 : 3), 140 mg. of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17α-ol is obtained as an oily product. [α]D 20 = -105°.

Workup

  1. customAt 0° C.
  2. washwashed neutral
  3. dry with materialdried over sodium sulfate
  4. customAfter purifying the crude product by preparative layer chromatography (system: hexane/ethyl acetate = 7 : 3), 140 mg

Sources & evidence

ORD record
ord-f7fe35d724a4432cb5be9f9604894edc
Source dataset
uspto-grants-1977_04
Patent number
US04016269

Reaction notes

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