Tetrahydrofuran → HCID 67484766, compound

HRID 2233358Notes

Reaction equation

HRID 2233358 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[CH:10]=[C:9]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:7]=2[CH:8]=1.C1COCC1>CO>[CH3:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[C:9]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67484700HCID 67484700, compound

Product 1

HCID 67484766HCID 67484766, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide solution (2.28 ml of 1M, 2.28 mmol, 3 eq) was added to a solution of 2-methyl-4-isobutoxy-6-methoxycarbonylbenzofuran (Method 7; 200 mg, 0.76 mmol; contained ca 15 mol % of isobutyl ester) in MeOH (2.28 ml)/THF (2.28 ml). After 2 hours at 50° C. the reaction mixture was stirred at ambient temperature overnight and then concentrated to half-volume in vacuo. The resulting solution was diluted with water and acidified to pH 5 (1M HCl), and the resulting flocculent precipitate filtered and dried to give the title compound as a colourless solid (165 mg, 88%). NMR: 1.02 (d, 6H), 2.06 (sept, 1H), 2.45 (s, 3H), 3.90 (d, 2H), 6.64 (s, 1H), 7.24 (s, 1H), 7.64 (s, 1H), 12.83 (bs, 1H); m/z 247 (M−H)−, 94.6% by LC-MS.

Workup

  1. concentrationconcentrated to half-volume in vacuo
  2. additionThe resulting solution was diluted with water
  3. filtrationthe resulting flocculent precipitate filtered
  4. customdried

Sources & evidence

ORD record
ord-e43ae9de972146ddb577f1cb4226490d
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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