Triphenylphosphine → HCID 58629864, compound

HRID 1391797Notes

Reaction equation

HRID 1391797 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:23]([CH3:34])[CH:22]=1.[Br:35][C:36]1[N:41]=[C:40]([CH:42](O)[CH2:43][O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[CH:39]=[CH:38][CH:37]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:35][C:36]1[N:41]=[C:40]([CH:42]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:23]([CH3:34])[CH:22]=2)[CH2:43][O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 58629911HCID 58629911, compound

Product 1

HCID 58629864HCID 58629864, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Ph3P (1.10 g, 4.19 mmol) in dry THF (30 mL), was treated with ethyl [(4-hydroxy-2-methylphenyl)oxy]acetate (696 mg, 3.31 mmol) and 1-(6-bromo-2-pyridinyl)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethanol (1.00 g, 3.01 mmol) and the resulting solution cooled to 0° C. (ice/water bath) under nitrogen. DIAD (0.829 ml, 4.21 mmol) in THF (30 ml) was then added drop-wise over 2 h using a syringe pump. The resulting mixture was then allowed to warm to ambient temperature over 22.5 h and was then reduced under vacuum to give an orange oily residue. Purification by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient, 1:1 to 0:1) afforded the title compound (429 mg).

Workup

  1. customto give an orange oily residue
  2. customPurification by SPE (silica, 10 g cartridge)
  3. washeluting with cyclohexane

Sources & evidence

ORD record
ord-b301027cc90e4236acbb6ad6194d1580
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…