Methyl formate → HCID 86605476, compound

HRID 2103004Notes

Reaction equation

HRID 2103004 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=[O:20].[H-].[Na+].[CH:24](OC)=[O:25]>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:11][CH2:12][CH2:13]1)[CH:9]([CH:24]=[O:25])[C:8]2=[O:20]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 69054496HCID 69054496, compound

Product 1

HCID 86605476HCID 86605476, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(methoxymethoxy)--5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one (2.0 g) in 20 mL of THF was added under stirring, NaH (1.38 g). After 5 minutes, 8.5 mL of methyl formate (137.4 mmol) were added dropwise to the mixture. The reaction was allowed to stir at room temperature overnight. The organic phase was washed with 1N HCl and water, dried over anhydrous MgSO4, and concentrated in vacuo to give 6-(methoxymethoxy)-5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-3-carbaldehyde as a yellow paste. This intermediate was used directly for subsequent reactions without further purification.

Workup

  1. stirringto stir at room temperature overnight
  2. washThe organic phase was washed with 1N HCl and water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b18583ccf8314f64a96d78d0f28b036e
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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