Acetaldehyde → HCID 178477243, compound

HRID 868490Notes

Reaction equation

HRID 868490 reaction equation
[Cl-].[Cl-].[CH:3]([O:6][Ti+2:7][O:8][CH:9]([CH3:11])[CH3:10])([CH3:5])[CH3:4].[CH:12](=[O:14])[CH3:13].C1C[O:18][CH2:17][CH2:16]1>>[CH:3]([O:6][Ti:7]([O:8][CH:9]([CH3:11])[CH3:10])([O:18][CH:17]=[CH2:16])[O:14][CH:12]=[CH2:13])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 8028Tetrahydrofuran2×HCID 178460659HCID 178460659, compound

Product 1

HCID 178477243HCID 178477243, compound

Procedure

Diisopropoxytitanium dichloride (0.262 g, 1.10 mmol) was dissolved in 20 ml of THF (dry, nitrogen atmosphere) in a 100 ml Schlenk flask. This solution was cooled to -78° C. at which point the lithium enolate of acetaldehyde, CH2 =CHOLi, in THF solution (2.20 mmol) was added to the stirred solution via syringe. This solution was allowed to warm to room temperature. After two hours of stirring, the solvent was evaporated by trap-to-trap distillation, leaving a yellow solid. This solid was extracted with pentane yielding a yellow pentane-soluble solid (crude yield 0.19 g, 70%). 1H NRM (CDCl3) δ 1.19 (d, J=6.4 Hz, 6.7H, CH--(CH3)2), 3.10 (d, J=28 Hz, 1H, OCH=CH2), 3.62 (s, 1H, OCH=CH2), 4.00 (sept, J=6.45 Hz, 1H, CH--(CH3)2), 6.55 (d, J=10.3 Hz, 1H, OCH=CH2), 7.01 (d, J=19.7, 1H, OCH=CH2).

Workup

  1. customthe solvent was evaporated by trap-to-trap
  2. distillationdistillation
  3. customleaving a yellow solid
  4. extractionThis solid was extracted with pentane yielding a yellow pentane-soluble solid (crude yield 0.19 g, 70%)

Sources & evidence

ORD record
ord-4f35ce40b0c04908b6f0321fd4497b53
Source dataset
uspto-grants-1988_10
Patent number
US04780337

Reaction notes

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