Propanal → HCID 57112010, compound

HRID 1781553Notes

Reaction equation

HRID 1781553 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1CC=O.C(=[O:31])CC.[C:32]1([CH3:38])[CH:37]=CC=[CH:34][CH:33]=1>>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[C:4]=1[CH2:34][CH:33]=[C:32]([CH3:38])[CH:37]=[O:31]

Participants

4

Reactant 3

HCID 527PropanalHCID 1140TolueneHCID 19046423HCID 19046423, compound

Product 1

HCID 57112010HCID 57112010, compound

Procedure

A solution of 2-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)acetaldehyde (10.0 g) and 2-triphenylphosphoranylidine propionaldehyde (10.3 g) in toluene (150 mL) was heated under nitrogen atmosphere using an oil bath at 80° C. After allowing the reaction to proceed for 16 hours, the mixture was cooled to ambient temperature and subjected to flash chromatography three times (7/2/1 hexanes/methylene chloride/methanol; 6/3/1 hexanes/methylene chloride/methanol; 1/1/1 hexanes/methylene chloride/ether). The residual solid (5.56 g) was recrystallized from ethyl acetate (200 mL) to afford 4-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranyl)2-methylbut-2-enaldehyde (2.65 g), m.p. 168.3°-173.2° C., impure with the starting aldehyde.

Workup

  1. customat 80° C
  2. customthe reaction
  3. customThe residual solid (5.56 g) was recrystallized from ethyl acetate (200 mL)

Sources & evidence

ORD record
ord-9607c20c20c74c6fbe9c3af9fb2b3115
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

Loading…