Water → (R)-2-(benzyloxymethyl)-3-methylbutan-1-ol

HRID 660378Notes

Reaction equation

HRID 660378 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][C@H:16]([CH:20]([CH3:22])[CH3:21])[C:17](O)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([O:14][CH2:15][C@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][OH:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 11492274(S)-2-(benzyloxymethyl)-3-methylbutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 68782329(R)-2-(benzyloxymethyl)-3-methylbutan-1-olYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension solution of LiAlH4 (28.5 g, 0.75 mol) in anhydrous THF (1 L) at 0° C. under N2 was added dropwise over 30 min a solution of (S)-2-(benzyloxymethyl)-3-methylbutanoic acid (66 g, 0.30 mol) in anhydrous THF (500 mL). The reaction mixture was warmed to rt and stirred overnight. After the mixture was cooled to 0° C., water (29 mL) was added dropwise, followed by 10% aq NaOH (29 mL). The mixture was filtered and the filtrate was evaporated. The residue was partitioned between EtOAc and water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give (R)-2-(benzyloxymethyl)-3-methylbutan-1-ol (54 g, 86%). 1H NMR (400 MHz, CDCl3): 0.92 (m, 6H), 1.66 (m, 1H), 1.77 (m, 1H), 2.70 (brs, 1H), 3.59 (m, 4H), 4.51 (m, 2H), 7.30 (m, 5H).

Workup

  1. temperatureAfter the mixture was cooled to 0° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was partitioned between EtOAc and water
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a6734b5cab63477bbc42b822f3b48720
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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