(2R)-3-Benzyloxymethoxy-2-methyl-propionic acid methyl ester → (2R)-3-Benzyloxymethoxy-2-methyl-propan-1-ol

HRID 493059Notes

Reaction equation

HRID 493059 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH3:16])[CH2:5][O:6][CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:9]([O:8][CH2:7][O:6][CH2:5][C@H:4]([CH3:16])[CH2:3][OH:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10082905(2R)-3-Benzyloxymethoxy-2-methyl-propionic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 11805955(2R)-3-Benzyloxymethoxy-2-methyl-propan-1-olYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ester 2 (0.5 g, 2.1 mmol) in anhydrous THF (4 mL) was added dropwise to a suspension of lithium aluminum hydride (0.16 g, 4.2 mmol) in anhydrous THF (10 mL) at 0° C. The cooling bath was removed, and the reaction was stirred at room temperature overnight, quenched with cold water, and extracted with EtOAc. The solvents were removed in vacuum and the crude oil was purified by silica gel chromatography using hexane/EtOAc (8:2) as an eluent to afford oily diol 3 (0.29 g, 66%).

Workup

  1. customThe cooling bath was removed
  2. customquenched with cold water
  3. extractionextracted with EtOAc
  4. customThe solvents were removed in vacuum
  5. customthe crude oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1f9a45735dff4d48a12b89eb30b2f784
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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