Sodium Hydroxide → HCID 86735732, compound

HRID 372857Notes

Reaction equation

HRID 372857 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:17])[C:10]([CH3:16])([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][C:24]([O-:26])=[O:25].[OH-].[Na+]>CO>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:17])[C:10]([CH3:15])([CH3:16])[CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86735733HCID 86735733, compound

Product 1

HCID 86735732HCID 86735732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl trans, cis-7-[2-hydroxy-5-(3-hydroxy-4,4-dimethyl-1-octenyl)cyclopentyl]-5-heptenoate (0.536 g, Isomer B less polar epimer), described in Example 92, in methanol (5 ml) is added a solution of sodium hydroxide (10%, 1.32 ml). The mixture is stirred for 18 hr. The solvent is removed under reduced pressure and the residue taken up in water and extracted with ether. The aqueous liquor is then rendered acidic with HCl (10%, 1.32 ml). The precipitate is taken up with ether. The ether extract is washed with water, dried (Na2SO4) and the solvent is removed to yield the title compound, Isomer B less polar epimer, nmr (CDCl3) δ 0.84 (m, 9H), 3.80 (m, 1H), 4.23 (m, 1H), 5.27 (broad, 3H), 5.5 (m, 4H), (i.e., racemic trans, cis-7-[2α-hydroxy-4,4-dimethyl-1-octenyl)cyclopentyl]-5-heptenoic acid).

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-6c81b0b084bc443f99f0950ed8e5b36d
Source dataset
uspto-grants-1978_05
Patent number
US04092427

Reaction notes

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