Methanol → 3-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid methyl ester

HRID 356526Notes

Reaction equation

HRID 356526 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:25])([CH:22]([CH3:24])[CH3:23])[CH2:18][C:19]([OH:21])=[O:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]O>>[CH3:26][O:20][C:19](=[O:21])[CH2:18][C:17]([CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)([OH:25])[CH:22]([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 887MethanolHCID 187986573-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid

Product 1

HCID 537325303-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid methyl ester

Procedure

A solution of 3-[2-(4-benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid from Example RRRR (10.1 g, 29.5 mmol), MeOH (300 mL), and H2 SO4 (0.2 mL) was refluxed for 3 days. The reaction was stripped to dryness and the product was partitioned between ethyl acetate and 5% NaHCO3. The solution was dried (MgSO4), and concentrated to give the title compound.

Workup

  1. customwas refluxed for 3 days
  2. customthe product was partitioned between ethyl acetate and 5% NaHCO3
  3. dry with materialThe solution was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d2f19c55ad54de4b50a41d294bfa18b
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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