Triphenylphosphine → 2-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl)-5-(3-chlorophenyl)-2H-tetrazole

HRID 639826

Reaction equation

HRID 639826 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[CH:34]=[C:35]([C:39]2[N:40]=[N:41][NH:42][N:43]=2)[CH:36]=[CH:37][CH:38]=1.[Si:44]([O:51][CH2:52][CH2:53][CH:54](O)[CH3:55])([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>C1COCC1>[Si:44]([O:51][CH2:52][CH2:53][CH:54]([N:41]1[N:42]=[N:43][C:39]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([Cl:32])[CH:34]=2)=[N:40]1)[CH3:55])([C:47]([CH3:48])([CH3:49])[CH3:50])([CH3:45])[CH3:46]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5925205-(3-chlorophenyl)-2H-1,2,3,4-tetrazoleHCID 5462977Diethyl azodicarboxylateHCID 110199954-((tert-Butyldimethylsilyl)oxy)butan-2-ol

Product 1

HCID 684318752-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl)-5-(3-chlorophenyl)-2H-tetrazoleYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To triphenylphosphine (2.6 g, 10 mmol) in THF (50 mL) at 0° C. under argon, DEAD (1.6 mL, 10 mmol) added during 5 minutes. After stirring for 40 minutes at 0° C. 5-(3-chlorophenyl)-2H-tetrazole (0.90 g, 5 mmol) followed by a solution of 4-{[tert-butyl(dimethyl)silyl]oxy}butan-2-ol (1.53 g, 7.5 mmol) (Tett. 2003, 59, 4739-4748) in THF (5 mL) was added. Stirring at 0° C. for 10 minutes was followed by 21 h at r.t. The mixture was concentrated and purified by flash column chromatography (SiO2, Heptane-EtOAc 7:1) to give 1.8 g (98%) of the title compound.

Workup

  1. additionwas added
  2. stirringStirring at 0° C. for 10 minutes
  3. waitwas followed by 21 h at r.t
  4. concentrationThe mixture was concentrated
  5. custompurified by flash column chromatography (SiO2, Heptane-EtOAc 7:1)

Sources & evidence

ORD record
ord-daf21f08fdd8429988c900ab2611d222
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Linked notes

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