Benzoyl chloride → HCID 67183458, compound

HRID 1808717Notes

Reaction equation

HRID 1808717 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-d9fd53109f55434985b62033c7ae40e6
Source dataset
uspto-grants-2013_01
Patent number
US08361973B2

Reaction notes

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