Trimethylsilyldiazomethane → Methyl 4-prop-2-ynylcyclohexanecarboxylate

HRID 430392Notes

Reaction equation

HRID 430392 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]([CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)[C:9]#[CH:10]>CO.ClCCl>[CH2:8]([CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:1])=[O:18])[CH2:13][CH2:12]1)[C:9]#[CH:10]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 107971444-Prop-2-ynylcyclohexanecarboxylic acid

Product 1

HCID 10749876Methyl 4-prop-2-ynylcyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(Trimethylsilyl)diazomethane (2.0 M) solution in hexanes (1 mL, 2 mmol) was added to a solution of 5.4 (0.34 g, 2 mmol) in 15 mL of methanol:dichloromethane (3:7). The solvents were removed under reduced pressure resulting in 100% conversion of starting material to product. 1H NMR (300 MHz, CDCl3) δ2.24 (dt, J=3.66, 12.1 Hz, 1H), 2.10 (dd, J=2.7, 6.5 Hz, 2H), 2.06 (dd, J=1.54, 6.54 Hz, 1H), 2.00-1.89 (m, 3H), 1.76 (d, J=2.3 Hz, 1H), 1.43 (dq, J=3.28, 13.1 Hz, 2H), 1.03 (dq, J=3.28, 13.1 Hz, 2H). 13C NMR (300 MHz, CDCl3) δ176.8, 83.3, 69.8, 51.9, 43.4, 36.7, 31.9, 29.2, 26.3.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customresulting in 100% conversion of starting material to product

Sources & evidence

ORD record
ord-81f6b0da7935417e901231bf35c680c4
Source dataset
uspto-grants-2001_11
Patent number
US06322771B1

Reaction notes

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