Trichloroacetic Acid → HCID 86745506, compound

HRID 1535054Notes

Reaction equation

HRID 1535054 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C:6]=2[CH:18]=1.C1([B:25](O)[OH:26])C=CC=CC=1.[C:28]1([CH2:34][CH2:35]CC=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl[C:40](Cl)(Cl)[C:41](O)=O>C1(C)C=CC=CC=1>[C:28]1([CH2:34][CH2:35][B:25]2[O:26][CH:7]([CH2:8][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]3[CH:18]=[C:2]4[O:1][CH:41]=[CH:40][C:3]4=[CH:4][C:5]=3[O:9]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 6421Trichloroacetic AcidHCID 290304-PhenylbutanalHCID 66827Phenylboronic AcidHCID 98812472-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-ol2×

Product 1

HCID 86745506HCID 86745506, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-hydroxy-2-(2-phenylethyl)-2,3-di-hydrobenzofuran, E5, (1.4 gm; 6 mmoles), phenyl-boronic acid (876 mgs; 7.2 mmoles), 4-phenylbutyraldehye (1.3 gm; 9 mmoles), trichloroacetic acid (300 mgs; 1.8 mmoles) and toluene (120 mL) was refluxed under nitrogen atmosphere for 7 hours and using a Dean Stark to collect azeotroped water. The mixture was cooled and stirred with saturated sodium bicarbonate solution. The toluene layer was separated, dried (MgSO4), filtered and concentrated to obtain 3.3 gm of crude 7,8-dihydro-2-(2-phenyl-7-(2-(2-phenylethyl)-4-(3-phenyl-propyl)-4H-furo[2,3-g]-1,3,2-benzodioxaborin, E28.

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 7 hours
  2. customto collect
  3. customazeotroped water
  4. temperatureThe mixture was cooled
  5. customThe toluene layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7163b183d51948da8e28fc0c60ec8094
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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