Tetrahydrofuran → HCID 66900381, compound

HRID 19396Notes

Reaction equation

HRID 19396 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([OH:20])[C:17]([OH:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1C[CH2:24][CH2:23][CH2:22]1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]2[CH2:17][O:19][C:23]([CH3:24])([CH3:22])[O:20]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 11818113(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

Product 1

HCID 66900381HCID 66900381, compoundYield 91%

Procedure

A solution of (S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid (3.1 g, 11.38 mmol) in tetrahydrofuran (50 mL) was treated with a solution of borane tetrahydrofuran complex in tetrahydrofuran (1.0 M, 22.7 mL, 22.76 mmol) at 0° C. The mixture was allowed to slowly warm to room temperature and stirred at this temperature for 2 h. The resulting mixture was carefully quenched with 1N aqueous sodium hydroxide and treated with ethyl acetate. The layers were separated and the aqueous layer extracted twice more with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was immediately treated with excess acetone dimethyl ketal and a catalytic amount of p-toluene sulfonic acid. The mixture was treated with ethyl acetate and water. The aqueous layer made basic with solid potassium carbonate (pH=9), and extracted with ethyl acetate. The organic layers were combined and dried over sodium sulfate, filtered and concentrated in vacuo which afforded (S)-4-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolane (3.1 g, 91%) as a white solid.

Workup

  1. customThe resulting mixture was carefully quenched with 1N aqueous sodium hydroxide
  2. additiontreated with ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted twice more with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe residue was immediately treated with excess acetone dimethyl ketal
  9. additionThe mixture was treated with ethyl acetate and water
  10. extractionextracted with ethyl acetate
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo which

Sources & evidence

ORD record
ord-270e7b470efa4a86b479d99c484b1be9
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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