Methane → HCID 86735947, compound

HRID 2419626Notes

Reaction equation

HRID 2419626 reaction equation
C([O:3][C:4](=[O:40])/[CH:5]=[CH:6]/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][C@@H:29]2[O:32]C(=O)C)[C@:25]2([CH3:26])[C@@H:20]([CH2:21][C@H:22]([O:36]C(=O)C)[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])C.[OH-].[Na+].C>O>[OH:36][C@@H:22]1[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@H:20]([CH2:19][CH2:18][C@@H:17]3[C@@H:27]2[CH2:28][C@H:29]([OH:32])[C@@:30]2([CH3:31])[C@H:16]3[CH2:15][CH2:14][C@@H:13]2[CH:11]([CH2:10]/[CH:9]=[CH:8]/[CH:7]=[CH:6]/[CH2:5][C:4]([OH:40])=[O:3])[CH3:12])[CH2:21]1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 86735948HCID 86735948, compound

Product 1

HCID 86735947HCID 86735947, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.25 g of 7-(3α,12α-diacetoxy-5β-pregnane-20-yl)-trans,trans-2,4-heptadienoic acid ethyl ester and 57 ml of 5N aqueous sodium hydroxide solution was stirred and refluxed for 1.5 hr. At the end of this time, 500 ml of water was added and the mixture heated to reflux. The cloudy solution was cooled, charcoal added and the mixture was filtered through a bed of diatomaceous earth. The filtrate was cooled to 0° and made acidic (pH3) by the dropwise addition of concentrated aqueous hydrochloric acid. The precipitate was filtered and air dried overnight under house vacuum. Crystallization from methyl ethyl ketone afforded 4 g of 7-(3α,12α-dihydroxy-5β-pregnane-20-yl)-trans,trans-3,5-heptadienoic acid, mp 208°-211°.

Workup

  1. temperaturerefluxed for 1.5 hr
  2. temperaturethe mixture heated to reflux
  3. temperatureThe cloudy solution was cooled
  4. filtrationthe mixture was filtered through a bed of diatomaceous earth
  5. temperatureThe filtrate was cooled to 0°
  6. additionby the dropwise addition of concentrated aqueous hydrochloric acid
  7. filtrationThe precipitate was filtered
  8. customair dried overnight under house vacuum
  9. customCrystallization from methyl ethyl ketone

Sources & evidence

ORD record
ord-eec12f834cb84a819ae2e8a740194f50
Source dataset
uspto-grants-1978_08
Patent number
US04107188

Reaction notes

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