Water → HCID 18653181, compound

HRID 1464823Notes

Reaction equation

HRID 1464823 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C@@H:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:9][CH2:8][C:7]=2[CH:20]=1)=[O:2].CC(C)([O-])C.[K+].[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br.O>CN(C=O)C>[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C@H:10]2[CH2:9][CH2:8][C:7]3[CH:20]=[C:3]([CH:1]=[O:2])[CH:4]=[CH:5][C:6]=3[O:11]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 680073-Fluorobenzyl bromideHCID 18653187HCID 18653187, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18653181HCID 18653181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-3,4-dihydro-6-formyl-2-(4-hydroxybenzyl)-2H-benzopyran (1.8 g, 6.7 mmol) in DMF (10 ml) at 0° C. was added potassium tertbutoxide (0.83 g, 7.4 mmol). After 30 minutes m-fluorobenzyl bromide (0.91 ml, 7.4 mmol) was added and the resulting slurry was warmed to room temperature and stirred for 2 hours. Water was added and the precipitate was collected, washed with water and air dried (2.5 g).

Workup

  1. customthe precipitate was collected
  2. washwashed with water and air
  3. customdried (2.5 g)

Sources & evidence

ORD record
ord-574a94b1d3904dba82d2c2198307061f
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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