Methanol → HCID 19848778, compound

HRID 1153908Notes

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

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 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

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

Sources & evidence

ORD record: ord-5577eca54d614325b4a3e2d5d356802a
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04486428

Reaction notes

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