tert-Butanol → HCID 22116011, compound

HRID 1885634Notes

Reaction equation

HRID 1885634 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.O[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:32][CH:31]([CH2:33][O:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=3)[CH2:30][C:29]2=[O:45])=[CH:24][CH:23]=1>C(Cl)Cl>[C:1]([O:5][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH2:32][CH:31]([CH2:33][O:34][C:35]3[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:43][CH:44]=3)[CH2:30][C:29]2=[O:45])=[CH:26][CH:27]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 10382682HCID 10382682, compound

Product 1

HCID 22116011HCID 22116011, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butanol (1.58 g), dicyclohexylcarbodiimide (4.04 g) and cuprous chloride (35 mg) are suspended in methylene chloride (5 ml) and the mixture is stirred at room temperature under shading for 4 days. Thereto is added a suspension of methyl 4-[1-(4-hydroxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate (1.52 g) in methylene chloride (30 ml) and the mixture is further stirred for 14 hours. The reaction mixture is concentrated under reduced pressure and thereto is added chloroform. The insoluble material is removed by filtration and the filtrate is subjected to silica gel column chromatography and eluted with chloroform to give the desired product (0.93 g), m.p. 126°-127.5° C.

Workup

  1. additionThereto is added
  2. stirringthe mixture is further stirred for 14 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionis added chloroform
  5. customThe insoluble material is removed by filtration
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-ba41547dd5594cc180463531c4f9a548
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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