Tetrahydrofuran → HCID 70615849, compound

HRID 2083794Notes

Reaction equation

HRID 2083794 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].O1CCCC1.[CH2:11]([O:13][C:14](=[O:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[C:25](=[CH:26][CH2:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:23][C@H:22]1[OH:35])[CH3:12].[NH4+].[Cl-]>C(OCC)C>[CH2:11]([O:13][C:14](=[O:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[C:25](=[CH:26][CH2:27][C:28]([OH:34])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:23][C@H:22]1[OH:35])[CH3:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 54372282HCID 54372282, compoundHCID 178418339Butyllithium

Product 1

HCID 70615849HCID 70615849, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.6 g. Butyl lithium, dissolved in 60 ml. tetrahydrofuran, is added dropwise to 3.7 g. 9β-hydroxy-15-oxo-12-prostenoic acid ethyl ester, dissolved in 150 ml. dry diethyl ether, with the exclusion of moisture, under argon and with stirring at -15°. The mixture is stirred for another hour, allowed to warm to 0° and mixed dropwise, with ice cooling, with 300 ml. saturated aqueous NH4Cl solution. The organic phase is separated, washed with water and dried over Na2SO4. The solvent is removed to obtain as residue 9β,15-dihydroxy-15-butyl-12-prostenoic acid ethyl ester.

Workup

  1. temperatureto warm to 0°
  2. additionmixed dropwise, with ice cooling, with 300 ml
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-2e016df11c144d92ba24725921a9a6bf
Source dataset
uspto-grants-1978_04
Patent number
US04086362

Reaction notes

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