Triphenylphosphine → (+/-)-Tert-butyl(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane
Reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:23])[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[C:4]([Si:1]([O:8][CH2:9][CH:10]1[O:23][C:13]2[C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[CH:20]=[CH:21][C:12]=2[CH2:11]1)([CH3:3])[CH3:2])([CH3:5])([CH3:6])[CH3:7]Participants
4
Procedure
Treatment of (±)-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-5,6,7,8-tetrahydronaphthalen-1-ol (5.75 g, 0.017 mol) with triphenylphosphine (4.71 g, 0.018 mol) and diethylazodicarboxylate (3.12 g, 0.018 mol) generally according to the procedure described for Intermediate 5 provided 4.38 g (80%) of (±)-tert-butyl(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane as a colorless oil. Rf=0.71 (silica, ethyl acetate:hexanes 1:5); Anal. calcd. for C19H30O2Si: C, 71.64; H, 9.49. Found: C, 71.4; H, 9.62.
Sources & evidence
- ORD record
- ord-0e62295c034c4eb9898e23bc02e79547
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
Loading…