Potassium Carbonate → HCID 131721745, compound

HRID 429452Notes

Reaction equation

HRID 429452 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C@H:13]([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[C@H:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:33][C:34]([O:36][CH3:37])=[O:35].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:37][O:36][C:34](=[O:35])[CH2:33][O:31][C:28]1[CH:27]=[CH:26][C:25]([C@H:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:10][CH:11]=3)[O:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 60984Methyl bromoacetateHCID 86755262HCID 86755262, compound

Product 1

HCID 131721745HCID 131721745, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(+,−) cis 4-(7-Benzyloxy-3-phenyl-chroman-4-yl)-phenol (0.5 g, 1.22 mmol), methyl bromoacetate (0.37 g, 2.44 mmol), 18-crown-6 (0.48 g, 1.83 mmol), and potassium carbonate 0.25 g, 1.83 mmol) was slurried in toluene (25 ml), and stirred at 100° C. for 75 min. After cooling the reaction mixture was filtered through a 1.6×6 cm silica column, eluted with 10% tetrahydrofuran in toluene and evaporated.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationwas filtered through a 1.6×6 cm silica column
  3. washeluted with 10% tetrahydrofuran in toluene
  4. customevaporated

Sources & evidence

ORD record
ord-ef0ed7f468bb462a91a2f1ee7328fb45
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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