4,7-Dihydro-2-isopropyl-1,3-dioxepin → HCID 20392493, compound

HRID 1863251Notes

Reaction equation

HRID 1863251 reaction equation
[CH2:1]([C:8]1O[C:10]([O:14]CC)=[C:11]([CH3:13])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([CH:20]1[O:26][CH2:25][CH:24]=[CH:23][CH2:22][O:21]1)([CH3:19])[CH3:18]>>[CH:17]([CH:20]1[O:26][CH2:25][C:24]2[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:12][C:11]([CH3:13])=[C:10]([OH:14])[C:23]=2[CH2:22][O:21]1)([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 794474,7-Dihydro-2-isopropyl-1,3-dioxepinHCID 20392505HCID 20392505, compound

Product 1

HCID 20392493HCID 20392493, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 12.6 g (60 millimoles) of 2-benzyl-4-methyl-5-ethoxy-oxazole and 42.6 g (300 millimoles) of 2-isopropyl-4,7-dihydro-1,3-dioxepine is heated for 5 hours at 180° C. On cooling the mixture in an ice bath, 4.2 g of 3-isopropyl-6-benzyl-8-methyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-ol crystallize out. A further 2.0 are obtained by evaporating the mother liquor, partitioning the residue between methylene chloride and dilute sodium hydroxide solution and neutralizing the alkaline phase. Recrystallization from ethyl acetate gives a pure product, of melting point 193°-194° C.

Workup

  1. temperatureOn cooling the mixture in an ice bath
  2. custom4.2 g of 3-isopropyl-6-benzyl-8-methyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-ol crystallize out
  3. customA further 2.0 are obtained
  4. customby evaporating the mother liquor
  5. custompartitioning the residue between methylene chloride and dilute sodium hydroxide solution
  6. customRecrystallization from ethyl acetate
  7. customgives a pure product

Sources & evidence

ORD record
ord-ade8e962637741839edf526e2e4c9229
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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