Diethyl Ether → HCID 13044106, compound

HRID 1701486Notes

Reaction equation

HRID 1701486 reaction equation
C([O:4][C@@H:5]1[C@@:31]2([CH3:32])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:33])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:26])[CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:8][C@@H:7]([O:34]C(=O)C)[CH2:6]1)(=O)C.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)(=O)C>[OH:4][C@@H:5]1[C@@:31]2([CH3:32])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:33])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:26])[CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:8][C@@H:7]([OH:34])[CH2:6]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13044109HCID 13044109, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13044106HCID 13044106, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.5 g. of (20S)-1α,3β-diacetoxy-20-methyl-21-tetrahydropyranyloxypregna-5-ene in 25 ml. of absolute ether was added 0.3 g. of lithium aluminum hydride and the suspension was stirred at room temperature for 1 hour. After cooling to 0°, 2 ml. of ethyl acetate was added and the mixture poured onto ice-water. The insoluble part was extracted with ethyl acetate, the organic solution was washed with water and dried over sodium sulfate. By filtration and evaporation under vacuum 1.4 g. of crystalline (20S)-1α,3β-dihydroxy-20-methyl-21-tetrahydropyranyloxypregna-5-ene was obtained. Recrystallization from methanol gave white crystals, m.p. 138°-141°; [α]D =-48.8° (c=0.5, chloroform).

Workup

  1. temperatureAfter cooling to 0°
  2. additionthe mixture poured onto ice-water
  3. extractionThe insoluble part was extracted with ethyl acetate
  4. washthe organic solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationBy filtration and evaporation under vacuum 1.4 g

Sources & evidence

ORD record
ord-a4dd4327aa554f108652307f031698c2
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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