Triphenylphosphine → 2-(4-(tert-Butyldimethylsilyloxy)butoxy)-3-chlorobenzaldehyde

HRID 84969

Reaction equation

HRID 84969 reaction equation
[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Si:11]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]O)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O>O1CCCC1>[Si:11]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:10][C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-olHCID 5196513-Chloro-2-hydroxybenzaldehydeHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate

Product 1

HCID 866534682-(4-(tert-Butyldimethylsilyloxy)butoxy)-3-chlorobenzaldehydeYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-chloro-2-hydroxybenzaldehyde (313 mg, 2 mmol) in tetrahydrofuran (4 mL) was added 4-(tert-butyldimethylsilyloxy)butan-1-ol (409 mg, 2 mmol), triphenylphosphine (524 mg, 2 mmol), and (E)-di-tert-butyl diazene-1,2-dicarboxylate (460 mg, 2 mmol). The mixture was stirred for 20 minutes and was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (4:1) to afford the titled compound (170 mg; 25%).

Workup

  1. customwas purified by silica gel column chromatography
  2. washeluting with hexanes and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-e14248c666b646bb9552482dd90aec97
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Linked notes

Loading…