Diazomethane → Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

HRID 1581113Notes

Reaction equation

HRID 1581113 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]1[CH2:9][CH2:8][CH:7]([CH:10]=[CH:11][CH:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26]>C(OCC)C>[OH:4][CH:5]1[CH2:9][CH2:8][CH:7]([CH:10]=[CH:11][CH:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:3])=[O:26]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 53394177HCID 53394177, compound

Product 1

HCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (0.327 g.) in dry diethyl ether (10 ml.) was added to a solution of 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid (0.4 g.) [prepared as described in Example 1] in dry diethyl ether (10 ml.). The resulting solution was allowed to stand at ambient temperature for 18 hours, during which time a solid precipitated. The solid was removed by filtration and the filtrate evaporated. The remaining traces of ether were removed from the residue by pumping under high vacuum to give methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (0.3 g., 72%). (Found: C, 70.8; H, 10.6. C21H38O4 requires C, 71.25; H, 10.72%) νmax 1730 cm-1, 980 cm-1 (liquid film). N.M.R. (approximately 10% solution in deuterochloroform) 0.92δ (triplet J=5c/s, terminal CH3) 1.7, 1.4δ (overlapping multiplets, cyclic and chain CH2), 2.38δ (triplet J=6.5c/s, CH2C=0), 2.70δ (broad singlet, --OH), 3.76δ (singlet --COOCH3), 4.32, 4.15 and 4.00δ (overlapping multiplets, cis and trans ##EQU7## 5.62δ (multiplet, ##EQU8##

Workup

  1. customa solid precipitated
  2. customThe solid was removed by filtration
  3. customthe filtrate evaporated
  4. customThe remaining traces of ether were removed from the residue

Sources & evidence

ORD record
ord-ebc883c31853454bb3abd4459e330391
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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