Dimethylformamide → HCID 11402394, compound

HRID 2250304Notes

Reaction equation

HRID 2250304 reaction equation
Br[C:2]1([CH3:19])[O:6][C:5]([CH3:17])([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]4)[CH2:8]2)[CH2:14]3)[O:4][C:3]1=[O:18].CN(C)C=O.C(OC(C)C)(C)C>>[CH2:19]=[C:2]1[O:6][C:5]([C:7]23[CH2:14][CH:13]4[CH2:15][CH:9]([CH2:10][CH:11]([CH2:12]4)[CH2:16]2)[CH2:8]3)([CH3:17])[O:4][C:3]1=[O:18]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7914Diisopropyl EtherHCID 11267468HCID 11267468, compound

Product 1

HCID 11402394HCID 11402394, compoundYield 88%

Conditions

Temperature
40 °C

Procedure

16.5 g (0.05 mol) of the obtained 5-bromo-2,5-dimethyl-2-(1-adamantyl)-1,3-dioxolan-4-one was placed in a 100 ml egg-plant type flask, and 73.1 g (1.0 mol) of N,N-dimethylformamide was added thereto, followed by intensively stirring at 40° C. for 2 hours. After completion of the stirring, the mixture was transferred into a 500 ml separatory funnel, and 200 g of isopropyl ether was added thereto, followed by fully shaking. Thereafter, the obtained mixture was left at rest, so as to separate the mixture into two layers. And then, the N,N-dimethylformamide phase that was a lower layer was removed. The isopropyl ether phase that was a upper layer washed with water to remove N,N-dimethylformamide dissolved therein. Thereafter, isopropyl ether was removed, so as to obtain white crystals. The obtained white crystals were recrystallized from hexane, so as to obtain 10.9 g of 5-methylene-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one at a purity of 99.8% (Formula (19), yield: 88%).

Workup

  1. customAfter completion of the stirring, the mixture was transferred into a 500 ml separatory funnel
  2. stirringby fully shaking
  3. waitThereafter, the obtained mixture was left at rest
  4. customso as to separate the mixture into two layers
  5. customwas removed
  6. washwashed with water
  7. customto remove N,N-dimethylformamide
  8. dissolutiondissolved
  9. customThereafter, isopropyl ether was removed
  10. customso as to obtain white crystals
  11. customThe obtained white crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-25262b35aa98499ab1fba0c06e3a9a2b
Source dataset
uspto-grants-2008_01
Patent number
US07316884B2

Reaction notes

Loading…