Methanol → HCID 57278482, compound

HRID 18814

Reaction equation

HRID 18814 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-].CO>ClCCl.CCOCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16]

Participants

7

Reactant 3

HCID 887MethanolHCID 7507CyclohexanemethanolHCID 12192Ethyl diazoacetate

Product 1

HCID 57278482HCID 57278482, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclohexylmethanol (1.23 mL, 10.0 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at RT for 30 min. To the reaction mixture is added MeOH, and the reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at to give 2.02 g of the product 419. 1H NMR (CDCl3) δ 4.22 (q, 2 H), 4.05 (s, 2 H), 3.33 (d, 2 H), 1.8-1.5 (m, 7 H), 1.4-1.1 (m, 5 H), 1.1-0.9 (m, 2 H); MS: m/z 200 (M++1).

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at

Sources & evidence

ORD record
ord-95be94d797e54a1cbb6ae47686dc6060
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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