Water → HCID 86752559, compound

HRID 1290330Notes

Reaction equation

HRID 1290330 reaction equation
OC1C=CC([CH:8]([CH:16]2[CH2:20]C[CH2:18][CH2:17]2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=CC=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.O.CN([CH:34]=[O:35])C>>[Cl:21][C:22]1[C:23]([O:35][CH2:34][C:22]2[CH:23]=[CH:24][CH:27]=[CH:28][CH:29]=2)=[C:24]([CH:25]2[CH2:18][CH2:17][CH:16]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:20]2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 19072522HCID 19072522, compound

Product 1

HCID 86752559HCID 86752559, compound

Procedure

1 g of tert-butyl 2-(4-hydroxyphenyl)-2-cyclopentyl-acetate (U.S. Pat. No. 834,734) and 1.2 ml of 3-chlorobenzyl bromide are dissolved in 10 ml of DMF and heated at 60°-70° C. for 14 h with 0.9 g of K2 CO3. After cooling, the mixture is treated with water and extracted by shaking with ether and the ether extract is dried. 1.3 g of the title compound are obtained as an oil. Rf =0.48 (cyclohexane / ethyl acetate 9:1)

Workup

  1. temperatureheated at 60°-70° C. for 14 h with 0.9 g of K2 CO3
  2. temperatureAfter cooling
  3. extractionextracted
  4. extractionthe ether extract
  5. customis dried

Sources & evidence

ORD record
ord-cacaa2370ed0463a9a7c7b8790efc873
Source dataset
uspto-grants-1998_05
Patent number
US05750783

Reaction notes

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