Tetrahydrofuran → HCID 86733500, compound

HRID 1657367Notes

Reaction equation

HRID 1657367 reaction equation
O1CCCCC1[O:7][C:8]1[CH:32]=[CH:31][C:30]2[C@@H:29]3[C@H:13]([C@H:14]4[C@@](C[CH2:28]3)(COC3CCCCO3)C(=O)[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]=2[CH:9]=1.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1.[H-].[C:40]([O:44][Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>CCOCC>[OH:7][C:8]1[CH:32]=[CH:31][C:30]2[C@@H:29]3[C@H:13]([C@H:14]4[C@@:34]([CH2:35][CH2:28]3)([CH2:40][OH:44])[C@@H:38]([O:37][CH3:36])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 681442863,18-Bis(tetrahydropyranyloxy)-1,3,5(10)-estratrien-17-one

Product 1

HCID 86733500HCID 86733500, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 450 mg. of 3,18-bis(tetrahydropyranyloxy)-1,3,5(10)-estratrien-17-one in 10 ml. of absolute THF is combined at 0° C. with 500 mg. of lithium tri-tert.-butoxyaluminum hydride and agitated for one-half hour at room temperature. Then, the mixture is poured into ice water, taken up in ether, washed neutral with water, dried, and evaporated. The residue of crude 3,18-bis(tetrahydropyranyloxy)-1,3,5(10)-estratrien-17β-ol is dissolved in 5 ml. of DMF, and under N2 100 mg. of sodium hydride (50% suspension in oil) is added thereto. After 1 hour of agitation at room temperature, 0.19 ml. of dimethyl sulfate is added. The mixture is stirred for another hour and then introduced into water. After extraction with ether, the organic phase is washed with water and dried. The residue of 3,18-bis(tetrahydropyranyloxy)-17β-methoxy-1,3,5(10)-estratriene remaining after evaporation is heated to the boiling point in 4 ml. of methanol with 4 ml. of water and 0.4 g. of oxalic acid. After 1 hour, the mixture is taken up in ether, washed neutral with water, dried, and evaporated, and after purification by chromatography over silica gel, 3,18-dihydroxy-17β-methoxy-1,3,5(10)-estratriene is produced.

Workup

  1. customis combined at 0° C. with 500 mg
  2. washwashed neutral with water
  3. customdried
  4. customevaporated
  5. dissolutionThe residue of crude 3,18-bis(tetrahydropyranyloxy)-1,3,5(10)-estratrien-17β-ol is dissolved in 5 ml
  6. additionof sodium hydride (50% suspension in oil) is added
  7. additionof dimethyl sulfate is added
  8. additionintroduced into water
  9. extractionAfter extraction with ether
  10. washthe organic phase is washed with water
  11. customdried
  12. customThe residue of 3,18-bis(tetrahydropyranyloxy)-17β-methoxy-1,3,5(10)-estratriene remaining after evaporation
  13. temperatureis heated to the boiling point in 4 ml
  14. waitAfter 1 hour
  15. washwashed neutral with water
  16. customdried
  17. customevaporated
  18. customafter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-e0d51ed94fde463fb4f8af5dcc6abdbc
Source dataset
uspto-grants-1976_06
Patent number
US03960841

Reaction notes

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