Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate → Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}heptanoate

HRID 372128Notes

Reaction equation

HRID 372128 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][CH:10]([CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:9]1[CH2:31][CH2:32][CH:33]([O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[H][H]>C(O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[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][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 2

HCID 53768284Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoateHCID 178418361HCID 178418361, compound

Product 1

HCID 20354841Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}heptanoateYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate (6.1 g.) [prepared as described in (n) above] was dissolved in ethanol (100 ml.) and catalytically hydrogenated using a 5% palladium on charcoal catalyst, with a hydrogen pressure of 15 kg./cm2, at room temperature. The catalyst was then filtered off and the ethanol removed in vacuo to give ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}heptanoate (5.7 g.), which was used as starting material in the following preparation (p) of ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate without further purification.

Workup

  1. customat room temperature
  2. filtrationThe catalyst was then filtered off
  3. customthe ethanol removed in vacuo

Sources & evidence

ORD record
ord-bd8e0f4c95b54ac4ab699208d1225388
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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