Triethyl 2-fluoro-2-phosphonoacetate → ethyl (2E)-3-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate

HRID 2180494Notes

Reaction equation

HRID 2180494 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[CH2:16]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([CH:33]([CH3:35])[CH3:34])=[CH:26][C:27]([CH3:32])([CH3:31])[O:28]2)=[CH:23][C:22]=1[C:36](=O)[CH3:37])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([CH:33]([CH3:35])[CH3:34])=[CH:26][C:27]([CH3:32])([CH3:31])[O:28]2)=[CH:23][C:22]=1/[C:36](/[CH3:37])=[C:6](/[F:7])\[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 224909691-(7-Butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-ethanone2×

Product 1

HCID 86597833ethyl (2E)-3-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate

Procedure

Following General Procedure K, triethyl-2-fluoro-2-phosphonoacetate (0.44 mL, 1.75 mmol) and 1-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-ethanone (Compound 65, 184 mg, 0.58 mmol) were reacted to give the title compound as a pink oil after purification by flash chromatography (silica gel, 1:9 ethyl acetate/hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-395a0a395ed940b5bce528dde7887eb6
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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