Diazomethane → Methyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate

HRID 372137Notes

Reaction equation

HRID 372137 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]1[CH:9]([OH:10])[CH2:8][CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:6]1[CH2:20][CH2:21][CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(OCC)C>[OH:4][CH:5]1[CH:9]([OH:10])[CH2:8][CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:3])=[O:18])[CH:6]1[CH2:20][CH2:21][CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 203548487-[3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid

Product 1

HCID 20354835Methyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoateYield 83.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane (60 mg.) in diethyl ether (10 ml.) was added to 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid (0.3 g.; prepared as described in Example 1(q)) and the reaction mixture was left to stand for one day at room temperature. The polymethylenes formed as by-products of the reaction were removed by filtration and the filtrate was washed with dilute aqueous sodium carbonate solution. Evaporation of the ethereal solution gave crude methyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate (0.26 g.), νmax 3450 cm-1, 1730 cm-1.

Workup

  1. waitthe reaction mixture was left
  2. customThe polymethylenes formed as by-products of the reaction
  3. customwere removed by filtration
  4. washthe filtrate was washed with dilute aqueous sodium carbonate solution
  5. customEvaporation of the ethereal solution

Sources & evidence

ORD record
ord-be077b9ca2c049bd936b6ebb4d4490de
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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