Methanol → HCID 19848778, compound

HRID 1905129Notes

Reaction equation

HRID 1905129 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][C:10]2[C:12]([OH:28])=[CH:13][C:14]([O:16][CH:17]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:18])=[CH:15][C:9]=2[O:8][C:7]1([CH3:30])[CH3:29])#N.[OH-:31].[Na+].C[OH:34]>>[OH:28][C:12]1[C:10]2[CH2:11][CH:6]([CH2:5][CH2:4][CH2:3][C:1]([OH:34])=[O:31])[C:7]([CH3:30])([CH3:29])[O:8][C:9]=2[CH:15]=[C:14]([O:16][CH:17]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:18])[CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19848774HCID 19848774, compound

Product 1

HCID 19848778HCID 19848778, compound

Procedure

A mixture of 1.407 g (3.45 mmole) dl-3-(3-cyanopropyl)-5-hydroxy-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran, 50 ml methanol and 26 ml 1N sodium hydroxide was heated at reflux overnight. The methanol was evaporated and the aqueous residue washed with methylene chloride. The methylene chloride washings were extracted with 10 ml 1N sodium hydroxide, the combined aqueous layers acidified with hydrochloric acid, extracted with methylene chloride and the organic extracts dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to obtain 1.189 g of the title acid as a foam. Mass spectrum (m/e): 426 (M+) 280 (M-146), 139 (base).

Workup

  1. additionA mixture of 1.407 g (3.45 mmole)
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. customThe methanol was evaporated
  5. washthe aqueous residue washed with methylene chloride
  6. extractionThe methylene chloride washings were extracted with 10 ml 1N sodium hydroxide
  7. extractionextracted with methylene chloride
  8. dry with materialthe organic extracts dried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fd110dd5661449d6a910db9fd21b702e
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

Loading…