Benzoyl chloride → HCID 67183458, compound

HRID 2367950Notes

Reaction equation

HRID 2367950 reaction equation
[CH2:1]([C:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])=[O:5])[CH:2]=[CH2:3].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:1]([C:4]([C@:6]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C@@:8]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])=[O:5])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86660596HCID 86660596, compound

Product 1

HCID 67183458HCID 67183458, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-allyl-D-arabinose 32 (75 g, 394 mmol) was dissolved in pyridine (800 mL) at 0° C., benzoyl chloride (101 mL, 867 mmol) was added over 2 h by addition funnel and the reaction was stirred while warming to room temperature for 16 h. The solvent was removed in vacuo, and the resulting residue was purified by silica gel flash chromatography (4:1 Hexanes:EtOAc to 3:2 Hexanes:EtOAc) to give 33 as a thick oil (45 g, 113 mmol, 29%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by silica gel flash chromatography (4:1 Hexanes:EtOAc to 3:2 Hexanes:EtOAc)

Sources & evidence

ORD record
ord-3b0a698bf77e4cea9b58566130ba749c
Source dataset
uspto-grants-2014_04
Patent number
US08703723B2

Reaction notes

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