Allyl bromide → (1R,4S)-5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene

HRID 13931Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C@H:11]3[CH2:13][C@H:8]([CH2:9][CH2:10]3)[C:7]=2[C:6]([OH:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>>[CH2:21]([O:14][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[C@@H:8]1[CH2:13][C@H:11]2[CH2:10][CH2:9]1)[CH:22]=[CH2:23]

Participants

Reactant 3

HCID 7841Allyl bromide

HCID 11430Potassium Carbonate

HCID 68583997(1R*,4S*)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol

Product 1

HCID 68584256(1R*,4S*)-5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthaleneYield 89.1%

Procedure

Treatment of (1R*,4S*)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol (14.61 g, 0.077 mol) with potassium carbonate (31.84 g, 0.23 mol) and allyl bromide (10.68 g, 0.088 mol) generally according to the procedure described for Intermediate 1 provided 15.8 g (89%) of (1R*,4S*)-5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene as a colorless oil. Anal. calcd. for C15H18O2.0.3H2O: C, 76.44; H, 7.95. Found: C, 76.43; H, 7.79.

Sources & evidence

ORD record: ord-986f743b879e4cc68d1323426243372d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Reaction notes

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