1,4,7,10-Tetraoxacyclododecane → (3R,6R)-6-benzhydryl-tetrahydropyran-3-ol

HRID 1897933Notes

Reaction equation

HRID 1897933 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].C1OCCOCCOCCOC1>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

5

Reactant 3

HCID 92691,4,7,10-TetraoxacyclododecaneHCID 21226445Aluminium lithium hydrideHCID 86605348(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane

Product 1

HCID 66631749(3R,6R)-6-benzhydryl-tetrahydropyran-3-olYield 77%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Treatment of (1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28d (0.06 g, 0.23 mmol) with a suspension of LiAlH4 (0.06 g, 1.58 mmol) in pentane along with 12-crown-4 ether (0.31 g, 1.74 mmol) for 15 h at room temperature afforded (3R,6R)-6-benzhydryl-tetrahydropyran-3-ol 38 0.046 g (77%, [α]D=(+)74.9, c=1, MeOH).

Sources & evidence

ORD record
ord-96da21b425bf4d4eabc2275aae1e7c8c
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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