Phthalimide → N-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]-phthalimide

HRID 2223870Notes

Reaction equation

HRID 2223870 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28]O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][N:34]2[C:30](=[O:40])[C:31]3=[CH:39][CH:38]=[CH:37][CH:36]=[C:32]3[C:33]2=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

Product 1

HCID 59714868N-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]-phthalimideYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethanol (1.23 g), phthalimide (530 mg) and triphenylphosphine (1.10 g) were dissolved in tetrahydrofuran (15 mL) and stirred for 20 minutes. Diethyl azocarboxylate (0.57 mL) was then added to the solution, and it was stirred at room temperature for 18 hours. The solvent was distilled off under reduced pressure, and the resulting residue was purified by chromatography (silica gel, 15-20% ethyl acetate:hexane) to give the title compound (1.08 g).

Workup

  1. stirringwas stirred at room temperature for 18 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by chromatography (silica gel, 15-20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-e50cafab06694e1d853ebdf3bf76fb8d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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