Tetrahydrofuran → (6-Hydroxy-7-t-butyl-5-isopropyl-8-propylchroman-2-yl)acetic acid

HRID 54627

Reaction equation

HRID 54627 reaction equation
[H-].[Na+].C[O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].O[C:15]1(C)[CH2:24][CH2:23][C:22]2[C:17](=[C:18]([CH2:36][CH2:37][CH3:38])[C:19]([C:32]([CH3:35])([CH3:34])[CH3:33])=[C:20](CC([O-])=O)[C:21]=2[CH:25]([CH3:27])[CH3:26])[O:16]1.[O:40]1CCCC1>>[OH:40][C:20]1[C:21]([CH:25]([CH3:26])[CH3:27])=[C:22]2[C:17](=[C:18]([CH2:36][CH2:37][CH3:38])[C:19]=1[C:32]([CH3:34])([CH3:35])[CH3:33])[O:16][CH:15]([CH2:7][C:5]([OH:4])=[O:6])[CH2:24][CH2:23]2

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 1317182912-Hydroxy-2-methyl-7-t-butyl-5-isopropyl-8-propyl-chroman-6-yl-acetate

Product 1

HCID 54411785(6-Hydroxy-7-t-butyl-5-isopropyl-8-propylchroman-2-yl)acetic acid

Procedure

Suspend sodium hydride (47.2 g of 56% in mineral oil, 1.10 mol) in anhydrous tetrahydrofuran (1 L). Place under a nitrogen atmosphere and add, by dropwise addition, trimethyl phosphonoacetate (209.4 g, 1.15 mol). Stir the 25 minutes and add a solution of 2-hydroxy-2-methyl-7-t-butyl-5-isopropyl-8-propyl-chroman-6-yl-acetate (0.5 mol) in tetrahydrofuran (1 L). Stir at room temperature for 18 hour then heat at reflux for 4 hours. Cool, evaporate the solvent in vacuo and purify by chromatography to give the title compound.

Workup

  1. stirringStir at room temperature for 18 hour
  2. temperaturethen heat
  3. temperatureat reflux for 4 hours
  4. temperatureCool
  5. customevaporate the solvent in vacuo
  6. custompurify by chromatography

Sources & evidence

ORD record
ord-6ae32be3706d4970a99758b87e310087
Source dataset
uspto-grants-1997_04
Patent number
US05623052

Linked notes

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