1-Phenylethanol → HCID 89524851, compound

HRID 920276Notes

Reaction equation

HRID 920276 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:14][CH:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:14])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 74091-PhenylethanolHCID 11776TriphenylphosphineHCID 784192(3H)-Benzoxazolone, 6-nitro-HCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 89524851HCID 89524851, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 6-nitrobenzo[d]oxazol-2(3H)-one (40-1, 5 g, 27.8 mmol) in THF (139 ml) was added α-methylbenzylalcohol (3.7 g, 30.5 mmol), polymer-bound triphenylphosphine (27.7 g, 83 mmol), and DIAD (11.2 g, 55.5 mmol). The reaction was shaken for 1 h at rt, filtered, and concentrated to yield 6-nitro-3-(1-phenylethyl)benzo[d]oxazol-2(3H)-one (7.89 g, 27.8 mmol) which was taken on to the next step without further purification. LRMS C15H14N202 [M−79] calc 205.1, obs 205.4.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e737623e11ab47b193f50577f86de874
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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