Benzyl Alcohol → HCID 86676358, compound

HRID 2280818Notes

Reaction equation

HRID 2280818 reaction equation
[CH2:1]([C:3]1(C(O)=O)[CH2:7][CH:6]=[CH:5][CH2:4]1)[CH3:2].CC[N:13]([CH:17](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O1CCOCC1>[CH2:37]([O:44][C:17](=[O:27])[NH:13][C:3]1([CH2:1][CH3:2])[CH2:4][CH:5]=[CH:6][CH2:7]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44182001HCID 44182001, compound

Product 1

HCID 86676358HCID 86676358, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-ethylcyclopent-3-enecarboxylic acid (1.9 g, 13.6 mmol) in dioxane (30 mL) was added DIEA (5.3 g, 41 mmol), diphenyl phosphoryl azide (4.5 g, 16.3 mmol) and benzylalcohol (2.2 g, 20.4 mmol). The mixture was stirred at 80° C. overnight and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (2.5% ethyl acetate in petroleum ether) to give the title product. (1.3 g, 5.3 mmol, yield: 39%). MS (ESI) m/z=246.2 [M+1]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (2.5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0c7649e04d934c57ba6755c6043c5371
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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