Tetrahydrofuran → HCID 10220296, compound

HRID 1045127Notes

Reaction equation

HRID 1045127 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[Mg]Br.[Mg].Br[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18]C=CC=2)[CH:16]=1.C1([Mg]Br)C=CC=CC=1.C1C[O:36]CC1>>[C:1]1([C@H:18]([C:17]2[CH:22]=[CH:23][CH:24]=[CH:15][CH:16]=2)[OH:36])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 113722-BromonaphthaleneHCID 5462224MagnesiumHCID 178418255HCID 178418255, compoundHCID 178418423HCID 178418423, compound

Product 1

HCID 10220296HCID 10220296, compound

Procedure

An operation was carried out in the same manner as in Example 14, except that 0.63 mL (0.375 mmol) of 2-naphthylmagnesium bromide (0.60 mol/L) prepared from magnesium and 2-bromonaphthalene was used instead of the anhydrous THF solution of phenylmagnesium bromide. Thus, (S)-1-naphthylphenylmethanol was obtained. The conversion rate of the raw material was 99%, while the enantiomeric excess was 80% ee.

Sources & evidence

ORD record
ord-628445e991cc429aa4e4664b8dedbe58
Source dataset
uspto-grants-2013_10
Patent number
US08563786B2

Reaction notes

Loading…