HCID 15686893, compound → HCID 21904693, compound

HRID 398091Notes

Reaction equation

HRID 398091 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:15](OC)=[O:16])[C:8](=[CH:13][CH:14]=1)[C:9](OC)=[O:10])[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([CH2:9][OH:10])=[C:7]([CH2:15][OH:16])[CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 15686893HCID 15686893, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21904693HCID 21904693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 4-(allyloxy)phthalate [prepared according to Inouye, M.; Tsuchiya, K.; Kitao, T. Angew. Chem. 1992, 104, 198-200 (See also Angew. Chem., Int. Ed. Engl, 1992, 204-205)] (9.9 g, 38 mmol) was dissolved in THF (40 mL) and cooled to 0° C. before the dropwise addition of lithium aluminium hydride (1M in THF, 77 mL, 77 mmol) over 10 min. The mixture was then allowed to stir at room temperature for 3 h before being quenched cautiously by the addition of water (1.4 mL) followed by 2M NaOH (1.4 mL). Excess MgSO4 was then added followed by water until a granular precipitate formed (ca. 5 mL). The mixture was then filtered and evaporated to a brown oil (7.1 g, ca. 95%). 1H NMR showed the material to be of ca. 85% purity. It was used directly in the next stage without further purification; δH (CDCl3, 400 MHz) 2.63 (1H, brs), 2.91 (1H, brs), 4.52 (2H, m), 4.67 (4H, m), 5.26 (1H, dd), 5.38 (1H, dd), 5.97-6.09 (1H, m), 6.80 (1H, dd), 6.92 (1H, d), 7.22 (1H, d).

Workup

  1. custombefore being quenched cautiously by the addition of water (1.4 mL)
  2. additionExcess MgSO4 was then added
  3. customformed (ca. 5 mL)
  4. filtrationThe mixture was then filtered
  5. customevaporated to a brown oil (7.1 g, ca. 95%)
  6. customIt was used directly in the next stage without further purification

Sources & evidence

ORD record
ord-3cff2b029fdd4b5c8ce0f838dbf7a198
Source dataset
uspto-grants-2003_08
Patent number
US06610747B2

Reaction notes

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