Ethyl orthoformate → HCID 18357471, compound

HRID 428049Notes

Reaction equation

HRID 428049 reaction equation
[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[O:5][C:6]=1C=O.[CH:13]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])OCC>C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[O:5][C:6]=1[CH:13]([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 123372723-Bromo-1-benzofuran-2-carbaldehyde

Product 1

HCID 18357471HCID 18357471, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 2.6 g of 3-bromo-2-benzo[b]furancarboxaldehyde (see M. Cugnon de Sevricourt and M. Robba, Bull. Chim. Soc. Fr., 1977, 142) in 2.7 ml of triethyl orthoformate was added 33 mg of paraoluene sulfonic acid and the solution stirred at at roon temperature overnight. The solution was diluted with a 5% sodium carbonate solution and extracted with ether. The ether extracts were dried over sodium sulfate and evaporated to give 3-bromo-2-(diethoxymethyl)-benzo[b]furan as a liquid; 1H-NMR (200 MHz, CDCl3) d 5.76 (CHOEt).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether extracts were dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1d6541f8c0b24b33b7184dabcaf2c1f6
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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