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

HRID 442439ノート

反応式

HRID 442439 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-13579c8008d147788e11c5e100e6c8ad
出典データセット
uspto-grants-1977_08
特許番号
US04045467

反応ノート

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