Diazomethane → HCID 57194080, compound

HRID 2289373Notes

Reaction equation

HRID 2289373 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:12][C@@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:9]([OH:11])=[O:10].[N+](=[CH2:21])=[N-]>C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:12][C@@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:9]([O:11][CH3:21])=[O:10]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 70267654HCID 70267654, compound

Product 1

HCID 57194080HCID 57194080, compoundYield 171.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.17 g of (2R,4S)-2-tetrahydropyranyloxy-4-caprylic acid obtained in Step 7 in 100 ml of diethyl ether was cooled to -50° C., and 200 ml of a diethyl ether solution of 75.68 mmol of diazomethane was poured thereinto. The mixture was stirred at room temperature for 1 hour, and diethyl ether was removed from the reaction mixture by distillation to obtain 2.12 g (100%) of the titled compound.

Workup

  1. customdiethyl ether was removed from the reaction mixture by distillation

Sources & evidence

ORD record
ord-5a5c49c1faf74bf288eac46ce580735e
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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