1-Naphthol → (R)-3-(Naphthalen-1-yloxy)-1-phenylpropan-1-OL

HRID 486969Notes

Reaction equation

[C:1]1([CH:7]([OH:11])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C.[C:30]1(O)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>>[C:38]1([O:10][CH2:9][CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:11])[C:39]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:36][CH:37]=1

Participants

Reactant 5

HCID 70051-Naphthol

HCID 73974-Toluenesulfonyl chloride

HCID 8471Triethylamine

HCID 14798Sodium Hydroxide

HCID 5720591-Phenyl-1,3-propanediol

Product 1

HCID 54389813(R)-3-(Naphthalen-1-yloxy)-1-phenylpropan-1-OLYield 87%

Procedure

Using (R) 3-phenyl-1,3-dihydroxypropane, 1.05 equivalents of 4-toluenesulfonyl chloride, 0.05 equivalents of poly-DMAP™, and 2.0 equivalents of triethylamine, 1.0 equivalents of 1-naphthol, and 1.1 equivalents of 50% sodium hydroxide as in example I.C.1, an 87% yield of (R)-(-)-3-(1-naphthalenyloxy)-1-phenyl-1-propanol was obtained. (HPLC chiral purity, 98.6% ee)

Sources & evidence

ORD record: ord-e130a136740a4e68925468801f3a40bf
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292962

Reaction notes

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