Mesitylene → (1R,4S)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol

HRID 13932

Reaction equation

C([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[C@@H:7]1[CH2:17][C@H:10]2[CH2:9][CH2:8]1)C=C.[C:18]1(C)[CH:23]=C(C)C=C(C)[CH:19]=1>>[CH2:23]([C:14]1[CH:13]=[C:12]([O:15][CH3:16])[C:11]2[C@H:10]3[CH2:17][C@H:7]([CH2:8][CH2:9]3)[C:6]=2[C:5]=1[OH:4])[CH:18]=[CH2:19]

Participants

Reactant 2

HCID 7947Mesitylene

HCID 68584256(1R*,4S*)-5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene

Product 1

HCID 68583880(1R*,4S*)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-olYield 80%

Procedure

Treatment of (1R*,4S*)-5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene (15.8 g, 0.069 mol) in refluxing mesitylene generally according to the procedure described for Intermediate 1 gave 12.58 g (80%) of (1R*,4S*)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol as a colorless oil. Anal. calcd. for C20H22O.0.2H2O: C, 77.02; H, 7.93. Found: C, 76.68; H, 7.88.

Sources & evidence

ORD record: ord-b13fc06abfcf40eb8c81fec33e28e61c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Linked notes

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