Imidazole → (+/-)-1-[1-(Benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol

HRID 13918Notes

Reaction equation

HRID 13918 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:19][CH:20]([OH:23])[CH2:21][OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].N1C=CN=C1>>[CH2:1]([O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:19][CH:20]([OH:23])[CH2:21][O:22][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68583356(+/-)-3-[1-(Benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]propane-1,2-diol

Product 1

HCID 68583229(+/-)-1-[1-(Benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-olYield 61%

Procedure

Treatment of (±)-3-[1-(benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]propane-1,2-diol (9.6 g, 0.031 mol) with tert-butyldimethylsilyl chloride (4.86 g, 0.032 mol) and imidazole (2.51 g, 0.037 mol) generally according to the procedure described for Intermediate 3 afforded 7.93 g (61%) of (±)-1-[1-(benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol as a colorless oil. Rf=0.63 (silica, ethyl acetate:hexanes 1:3); 1H NMR (DMSO-d6) δH 7.48 (d, 2H); 7.35 (m, 3H); 7.03 (d, 1H); 6.78 (d, 1H); 4.77 (q, 2H); 4.55 (d, 1H); 3.75 (m, 1H); 3.45 (m, 2H); 2.85 (dd, 1H); 2.69 (m, 4H), 2.51 (dd, 1H); 1.68 (m, 4H); 0.8 (s, 9H); 0.0 (d, 6H).

Sources & evidence

ORD record
ord-9a0fc9afc98d480a90a8dae8a8050c3f
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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