Methane → HCID 86735944, compound

HRID 2419622Notes

Reaction equation

HRID 2419622 reaction equation
C[O:2][C:3](=[O:35])/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][C@@H:26]2[O:29]C=O)[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([O:32]C=O)[CH2:20][CH2:21]2)[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9].C>[OH-].[Na+]>[OH:32][C@@H:19]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:17]([CH2:16][CH2:15][C@@H:14]3[C@@H:24]2[CH2:25][C@H:26]([OH:29])[C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH2:7][CH2:6]/[CH:5]=[CH:4]/[C:3]([OH:35])=[O:2])[CH3:9])[CH2:18]1

Participants

4

Reactant 2

HCID 297MethaneHCID 86735945HCID 86735945, compound

Product 1

HCID 86735944HCID 86735944, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5.2 g of 5-(3α,12α-diformyloxy-5β-pregnane-20-yl)-trans-2-pentenoic acid methyl ester and 30 ml of 5 N aqueous sodium hydroxide was added and the mixture heated to reflux. The solution was then cooled, treated with charcoal and filtered with suction through a bed of diatomaceous earth. The filtrate was then cooled to 0° and with stirring was acidified to a pH3 by the dropwise addition of concentrated hydrochloric acid. The resulting precipitate was filtered and air dried overnight under house vacuum. Crystallization from methyl ethyl ketone gave 3 g of 5-(3α,12α-dihydroxy-5β-pregnane-20-yl)-trans-2-pentenoic acid, mp 204°-208°.

Workup

  1. additionwas added
  2. temperaturethe mixture heated to reflux
  3. temperatureThe solution was then cooled
  4. filtrationfiltered with suction through a bed of diatomaceous earth
  5. temperatureThe filtrate was then cooled to 0°
  6. additionwas acidified to a pH3 by the dropwise addition of concentrated hydrochloric acid
  7. filtrationThe resulting precipitate was filtered
  8. customair dried overnight under house vacuum
  9. customCrystallization from methyl ethyl ketone

Sources & evidence

ORD record
ord-8843791030ca4e6e9976777e8aa0ae91
Source dataset
uspto-grants-1978_08
Patent number
US04107188

Reaction notes

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