Hydrochloric Acid → Ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate

HRID 442439Notes

Reaction equation

HRID 442439 reaction equation
O1CCCCC1[O:7][CH:8]1[CH:12]([O:13]C2CCCCO2)[CH2:11][CH:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:9]1[CH2:31][CH2:32][CH:33]([O:39]C1CCCCO1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].Cl>C(O)C>[OH:7][CH:8]1[CH:12]([OH:13])[CH2:11][CH:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:9]1[CH2:31][CH2:32][CH:33]([OH:39])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20354841Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}heptanoate

Product 1

HCID 20354857Ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoateYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}heptanoate (5.5 g.) [prepared as described in (o) above], ethanol (100 ml.), N hydrochloric acid (100 ml.) and a cation-exchange resin [Dowex resin AG50W-X 8H+ (7.5 g.)] was stirred at 50°-60° C. for 18 hours. The mixture was then cooled and filtered and the solid washed with diethyl ether and water. The combined filtrate and washings were evaporated in vacuo to remove organic solvents and the aqueous residue extracted with diethyl ether. The ethereal extract was dried over anhydrous sodium carbonate and evaporated in vacuo to give ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate (3.2 g.), which was used as starting material in the following preparation (q) of 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid without further purification.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. washthe solid washed with diethyl ether and water
  4. customThe combined filtrate and washings were evaporated in vacuo
  5. customto remove organic solvents
  6. extractionthe aqueous residue extracted with diethyl ether
  7. extractionThe ethereal extract
  8. dry with materialwas dried over anhydrous sodium carbonate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-13579c8008d147788e11c5e100e6c8ad
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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