Tetrahydrofuran → (R)-Phenyl(p-tolyl)methanol

HRID 1045129Notes

Reaction equation

HRID 1045129 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[C:6]1([Mg]Br)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:14]1([Mg]C2C=CC=CC=2)[CH:19]=CC=C[CH:15]=1.O1CCOC[CH2:28]1>>[CH3:28][C:6]1[CH:11]=[CH:10][C:9]([C@H:5]([OH:4])[C:1]2[CH:19]=[CH:14][CH:15]=[CH:3][CH:2]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 178418255HCID 178418255, compoundHCID 178420449HCID 178420449, compound

Product 1

HCID 7003729(R)-Phenyl(p-tolyl)methanol

Procedure

An operation was carried out in the same manner as in Example 1, except that 0.40 mL (0.40 mmol) of an anhydrous THF solution (1.0 mol/L) of phenylmagnesium bromide was used instead of the anhydrous 1,4-dioxane solution of diphenylmagnesium. Thus, (R)-4-methylbenzhydrol was obtained. The conversion rate of the raw material was 98%, while the enantiomeric excess was 39% ee.

Sources & evidence

ORD record
ord-b06b146eaa6f4ae1b3da036c8094e0b9
Source dataset
uspto-grants-2013_10
Patent number
US08563786B2

Reaction notes

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