Hydrochloric Acid → HCID 22788009, compound

HRID 1578683Notes

Reaction equation

HRID 1578683 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C@@H:21]3[C@H:8]([C@H:9]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:12]3([CH:16]=[CH:15][CH2:14][O:13]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.B.[OH-:26].[Na+].OO.Cl>O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C@@H:21]3[C@H:8]([C@H:9]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:12]3([CH2:16][CH:15]([OH:26])[CH2:14][O:13]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 54246468HCID 54246468, compound

Product 1

HCID 22788009HCID 22788009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 116 parts of 3-methoxyspiro[estra-1,3,5(10)-triene-17,2'(5'H)-furan] in 1100 parts of tetrahydrofuran at 5°-10° under nitrogen is added, with stirring, a solution of approximately 5 parts of borane in 325 parts of tetrahydrofuran. Stirring at 5°-10° is continued for 21/4 hours, whereupon a solution of 26 parts of sodium hydroxide in 213 parts of water followed -- cautiously -- by 131 parts of 30% hydrogen peroxide is mixed in. The resultant mixture is acidified with 20% hydrochloric acid and then poured into 7000 parts of ice water. The precipitate which forms is isolated by filtration, washed with water, dried in air, and taken up in benzene. The benzene solution is chromatographed on silica gel, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvents. From an eluate comprising 10% ethyl acetate in benzene, on evaporation of solvent and recrystallization of the residue from ethyl acetate, 4' ,5'-dihydro-3-methoxyspiro[estra-1,3,5(10)-triene-17,2'(3'H)-furan]-4'-ol melting at 95°-97° is obtained.

Workup

  1. stirringStirring at 5°-10°
  2. custom4 hours
  3. customThe precipitate which forms is isolated by filtration
  4. washwashed with water
  5. customdried in air
  6. customThe benzene solution is chromatographed on silica gel
  7. customFrom an eluate comprising 10% ethyl acetate in benzene, on evaporation of solvent and recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-4fb1db7e1bc840d589f093f7404bea0b
Source dataset
uspto-grants-1976_02
Patent number
US03939155

Reaction notes

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