Trimethylsilyldiazomethane → HCID 178501284, compound

HRID 1035694Notes

Reaction equation

HRID 1035694 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[CH3:11][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178525779HCID 178525779, compound

Product 1

HCID 178501284HCID 178501284, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

2 g of cis-4-hydroxycyclohexanecarboxylic acid (13.87 mmol, 1 eq.) are placed in 50 mL of a 4/1 mixture of toluene/methanol at room temperature. Trimethylsilyl-diazomethane (111 mL, 221.96 mmol, 16 eq.) is poured into the reaction medium with stirring. After 3 hours at room temperature, the reaction medium is evaporated to give 2.6 g of methyl cis-4-hydroxycyclohexanecarboxylate.

Workup

  1. customthe reaction medium is evaporated

Sources & evidence

ORD record
ord-a17d6560d56b49ce8bc74aea7998ed5c
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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