Triphenylphosphine → (+/-)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane
Reaction equation
[Si:1]([O:8][CH2:9][CH:10](O)[CH2:11][C:12]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[OH:21])([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>O1CCCC1>[C:4]([Si:1]([CH3:2])([CH3:3])[O:8][CH2:9][CH:10]1[O:21][C:13]2[C:14]3[CH2:15][CH2:16][CH2:17][C:18]=3[CH:19]=[CH:20][C:12]=2[CH2:11]1)([CH3:5])([CH3:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol (6.78 g, 21.02 mmol) in tetrahydrofuran (210 mL) cooled to 0° C. was added triphenylphosphine (5.79 g, 22.07 mmol) followed by diethylazodicarboxylate (3.84 g, 22.07 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched by the addition of water (10 mL) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:7) provided 2.93 g (46%) of (±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane as a colorless oil. Rf=0.86 (silica, ethyl acetate:hexanes 1:5); Anal. calcd. for C18H28O2Si: C, 71.0; H, 9.27. Found: C, 69.77; H, 9.21.
Workup
- customThe reaction mixture was quenched by the addition of water (10 mL)
- customthe solvent was removed in vacuo
- customto give a crude solid
- customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:7)
Sources & evidence
- ORD record
- ord-74af17c71e4c45f0b64a7f4faf47ee5f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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