Lithium hydroxide, monohydrate → HCID 59346905, compound

HRID 20578Notes

Reaction equation

HRID 20578 reaction equation
O.[OH-].[Li+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:21]=1)[C:15]([O:17]C)=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.C1COCC1>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:21]=1)[C:15]([OH:17])=[O:16])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127090methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate

Product 1

HCID 59346905HCID 59346905, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (1.30 g, 0.03 mol) in water (40 mL) was added to a solution of methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate (4.11 g, 0.012 mol) in THF (80 mL) and the reaction mixture stirred for 20 hours at ambient temperature. The THF was removed in vacuo. The aqueous residue was adjusted to pH3 with 1M hydrochloric acid and extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4), filtered, and evaporated to give the desired compound (3.79 g).

Workup

  1. customThe THF was removed in vacuo
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ebb519a626cc41c4ab4cb6494984bf4f
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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