Water → HCID 68135586, compound

HRID 1578667Notes

Reaction equation

HRID 1578667 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C[O:6][C:7](=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:18]([O:19]C2CCCCO2)[CH2:17][CH2:16][CH:15]1/[CH:26]=[CH:27]/[CH:28](O)[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[OH2:38].O1CCC[CH2:40]1>C(O)(=O)C>[CH3:40][O:38][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:18]([OH:19])[CH2:17][CH2:16][CH:15]1/[CH:26]=[CH:27]/[CH:28]([O:3][C:1](=[O:4])[CH3:2])[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 86733058HCID 86733058, compound

Product 1

HCID 68135586HCID 68135586, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

trans-2-(4-Cyclohexyl-3-hydroxy-1-butenyl)-5-[(tetrahydropyran-2-yl)oxy]cyclopentaneheptanoic acid methyl ester acetate (44 g), described in Example 8, is dissolved in acetic acid (426 ml), water (212 ml) and tetrahydrofuran (35.7 ml). The mixture is stirred at 60°C (bath temperature) for 3 hr. The solvent is removed under reduced pressure. The residue is taken up in ether. The ether solution is washed with water, dried and evaporated to yield trans-2-(4-cyclohexyl-3-acetoxy-1-butenyl)-5-hydroxycyclopentaneheptanoic acid methyl ester νmaxCHCl3 3,451, 1,730, 1,240 cm-1.

Workup

  1. customThe solvent is removed under reduced pressure
  2. washThe ether solution is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-542d552642a64a32bbe6d264d4087b49
Source dataset
uspto-grants-1976_02
Patent number
US03937801

Reaction notes

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