Lithium Hydroxide → HCID 22600131, compound

HRID 1383374Notes

Reaction equation

HRID 1383374 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][OH:22])[C:16]([O:18]CC)=[O:17])=[CH:11][C:10]=1[O:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][OH:22])[C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[O:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22600079HCID 22600079, compound

Product 1

HCID 22600131HCID 22600131, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-benzyloxy-3-methoxyphenyl)-3-hydroxy-propionate (1.29 g; 3.29 mmol; from step (iii) above) in THF (12.5 mL) was added a solution of LiOH (0.273 g; 6.75 mmol) in H2O (5 mL), and the mixture was stirred at room temperature for 2.5 hours. The resultant mixture was partially concentrated, water (25 mL) was added, the mixture was washed with two portions of CH2Cl2, made acidic with HCl/aq (2M), and extracted with 3 portions of CH2Cl2. The combined organic layers were washed with brine, dried (Na2SO4), and evaporated to yield 10.55 g (quant.) of a yellow powder. Purity 83.2%. 1H-NMR (400 MHz; MeOH): δ 7.41 (d, 2H); 7.32 (m, 4H); 6.94 (d, 2H); 6.82 (dd, 1H); 5.06 (s, 2H); 4.04 (m, 1H); 3.83 (s, 3H); 3.70 (m, 2H).

Workup

  1. concentrationThe resultant mixture was partially concentrated
  2. additionwater (25 mL) was added
  3. washthe mixture was washed with two portions of CH2Cl2
  4. extractionextracted with 3 portions of CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto yield 10.55 g (quant.) of a yellow powder

Sources & evidence

ORD record
ord-56770ad2a4804d6db42a9bbbaa960ad5
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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