3-Furanmethanol, 5-(phenylmethyl)- → HCID 23634408, compound

HRID 2099548Notes

Reaction equation

HRID 2099548 reaction equation
[CH2:1]([C:8]1[O:12][CH:11]=[C:10]([CH2:13][OH:14])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:30])[C@@H:18](/[CH:19]=[C:20](/[F:26])\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@H:17]1[C:27](O)=[O:28]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:30][C:16]1([CH3:15])[C@@H:18](/[CH:19]=[C:20](/[F:26])\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@H:17]1[C:27]([O:14][CH2:13][C:10]1[CH:9]=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:12][CH:11]=1)=[O:28]

Participants

5

Reactant 2

HCID 123643963-Furanmethanol, 5-(phenylmethyl)-HCID 13041480HCID 13041480, compound

Product 1

HCID 23634408HCID 23634408, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, to a mixture of 0.50 g of 5-benzyl-3-furylmethyl alcohol, 0.62 g of (1R)-cis-2,2-dimethyl-3-((E)-3-ethoxy-2-fluoro-3-oxo-1-propenyl)-cyclopropanecarboxylic acid, 0.1 g of 4-dimethylaminopyridine and 7 ml of dichloromethane was added 0.60 g of N,N-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.69 g of 5-benzyl-3-furylmethyl (1R)-cis-2,2-dimethyl-3-((E)-3-ethoxy-2-fluoro-3-oxo-1-propenyl)cyclopropanecarboxylate (hereinafter, referred to as the present compound (1)).

Workup

  1. filtrationThen, the reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3005bc0a64543d6a1b11b4530b44d63
Source dataset
uspto-grants-2009_08
Patent number
US07569603B2

Reaction notes

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