Sodium borohydride → {4-[8-Hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester

HRID 898676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898676
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH:23]=[O:24])[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23][OH:24])[CH:22]=2)[O:19][C:18]([CH3:25])([CH3:26])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 59692068HCID 59692068, Verbindung2×

Produkt 1

HCID 59692069{4-[8-Hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred, cooled (ice bath) solution of {4-[8-formyl-2,2,4,4-tetramethyl chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 45, 0.21 g, 0.58 mmol) in methanol (4 mL) was treated with sodium borohydride (0.024 g, 0.64 mmol) and the resulting reaction mixture was stirred for 2 h. The reaction mixture was quenched with water and extracted with diethyl ether. The organic phase was washed with water (×1) and brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title product as a colorless oil (0.21 g, 100%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water (×1) and brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1707f1a75690442a9213101b7eb14f6d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351737B2

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