Aluminium lithium hydride → 2-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)ethanol

HRID 929155Notes

Reaction equation

HRID 929155 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Si:7]([O:14][C@H:15]1[C@H:19]2[O:20][CH2:21][CH:22]([CH2:23][C:24](OCC)=[O:25])[C@H:18]2[O:17][CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C1COCC1>[Si:7]([O:14][C@H:15]1[C@H:19]2[O:20][CH2:21][CH:22]([CH2:23][CH2:24][OH:25])[C@H:18]2[O:17][CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90042502ethyl 2-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)acetate

Product 1

HCID 900420242-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.077 ml, 1.077 mmol) was added to a stirred, cooled (0° C.) mixture of ethyl 2-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)acetate (178 mg, 0.539 mmol) in THF (5 ml) and the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with 1N NaOH (1 mL), stirred for 10 minutes, filtered through Celite™ and washed with EtOAc (50 mL). The solution was washed with brine (20 mL), dried (Na2SO4) and concentrated to dryness to give title compound. LC-MS: calculated for C14H28O4Si 288.18 observed m/e: 289.21 (M+H)+ (Rt 1.16/2 min)

Workup

  1. temperaturecooled
  2. customThe reaction mixture was quenched with 1N NaOH (1 mL)
  3. stirringstirred for 10 minutes
  4. filtrationfiltered through Celite™
  5. washwashed with EtOAc (50 mL)
  6. washThe solution was washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6b6cfe474d804617b26bfae98af35928
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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