Tetrahydrofurfuryl alcohol → HCID 67080952, compound

HRID 1021470Notes

Reaction equation

HRID 1021470 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][C:13]([C:15]3[CH:35]=[CH:34][C:18]([O:19][C:20]4[CH:29]=[C:28]5[C:23]([CH:24]([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][O:27]5)=[CH:22][C:21]=4[Cl:33])=[CH:17][CH:16]=3)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1.O1CCCC1CO.C[O-].[Na+:45]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][C:13]([C:15]3[CH:35]=[CH:34][C:18]([O:19][C:20]4[CH:29]=[C:28]5[C:23]([CH:24]([C:30]([O-:32])=[O:31])[CH2:25][CH2:26][O:27]5)=[CH:22][C:21]=4[Cl:33])=[CH:17][CH:16]=3)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[Na+:45]

Participants

4

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 10942334Sodium MethoxideHCID 67080881HCID 67080881, compound

Product 1

HCID 67080952HCID 67080952, compoundYield 101%

Procedure

7-(4-(2-(benzo[d][1,3]dioxol-5-yl)ethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylic acid (60 mg, 0.12 mmol), 0.1 molar in 4:1 tetrahydrofuran-methanol, was treated with sodium methanolate (242 μl, 0.12 mmol) at ambient temperature. After 15 minutes, the solvent was removed in vacuo. The resulting solid was taken up in ethyl acetate and concentrated in vacuo. The solid was then taken up in 4:1 dichloromethane-hexanes and concentrated in vacuo and dried under high vacuum to provide sodium 7-(4-(2-(benzo[d][1,3]dioxol-5-yl)ethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (63 mg, 0.12 mmol, 101% yield) as a solid. MS (apci) m/z=495.9 (M+2H-Na).

Workup

  1. customthe solvent was removed in vacuo
  2. concentrationconcentrated in vacuo
  3. concentrationconcentrated in vacuo
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-8ff723fdf9734ea9b5af75d8b1184790
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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