Aluminium lithium hydride → Trans-6-benzhydryl-tetrahydropyran-3-ol

HRID 78947Notes

Reaction equation

HRID 78947 reaction equation
[CH:1]([C@H:14]1[CH2:20][C@H:19]2[C@H:17]([O:18]2)[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCCCC>[CH:1]([C@@H:14]1[O:15][CH2:16][C@@H:17]([OH:18])[CH2:19][CH2:20]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86605347(1R,4R,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane

Product 1

HCID 11608697Trans-6-benzhydryl-tetrahydropyran-3-olYield 70%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

(1R,4R,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane (0.05 g, 0.19 mmol) was treated with LiAlH4 (0.036 g, 0.94 mmol) (Procedure I) in dry pentane to yield trans-(3S,6R)-6-benzhydryl-tetrahydro-pyran-3-ol 33b 0.035 g (70%, [α]D=(+)61.7, c=1, MeOH).

Sources & evidence

ORD record
ord-5822be276e24439c935abf218252ab2f
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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