Allyl bromide → 6-Allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol

HRID 13935

반응식

HRID 13935 반응식
[CH3:1][O:2][C:3]1[C:12]2[CH:11]3[CH2:13][CH2:14][CH:8]([CH2:9][CH2:10]3)[C:7]=2[C:6]([OH:15])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].C(OC1C=CC(OC)=C2C=1C1CCC2CC1)C=C.C(OCC=C)C=C.C1(C)C=C(C)C=C(C)C=1>>[CH2:24]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[CH:11]3[CH2:13][CH2:14][CH:8]([CH2:9][CH2:10]3)[C:7]=2[C:6]=1[OH:15])[CH:23]=[CH2:22]

참가 물질

7

실험 절차

Treatment of 8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol (11.30 g, 0.055 mol) with potassium carbonate (22.94 g, 0.166 mol) and allyl bromide (7.36 g, 0.061 mol) generally according to the procedure described for Intermediate 1 afforded 5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene. Treatment of the allyl ether in refluxing mesitylene generally according to the procedure described for Intermediate 1 gave 6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol. Treatment of the phenyl with potassium carbonate (20.04 g, 0.145 mol), benzyl bromide (9.09 g, 0.053 mol), and tetrabutylammonium iodide (1.79 g, 0.005 mol) generally according to the procedure described for Intermediate 1 provided 15.05 g (82%) of 6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene as a colorless oil. Anal. calcd. for C23H26O2.0.1H2O: C, 82.16; H, 7.85. Found: C, 81.98; H, 7.71.

출처 및 근거

ORD 기록
ord-3e3c474f987f403e9855d51ef8ddff57
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728155B2

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