2-Methoxy-5-(trifluoromethoxy)benzaldehyde → 2-Methoxy-5-(trifluoromethoxy)benzyl alcohol

HRID 349247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349247
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:15])[F:14])=[CH:7][C:4]=1[CH2:5][OH:6]

Komponenten

4

Edukt 2

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 50112462-Methoxy-5-(trifluoromethoxy)benzyl alcoholAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve 2-methoxy-5-trifluoromethoxy-benzaldehyde (9.0 g, 40.9 mmol) in MeOH (100 mL) and treat with sodium borohydride (1.45 g, 38.3 mmol). Stir at RT for 1 h., then carefully quench with 1N HCl to pH 3. Concentrate, then extract the aqueous mixture with CH2Cl2 (3×100 mL). Combine the organic phases and wash with saturated NaHCO3 (100 mL) and brine (100 mL). Dry the organic layer, then filter, and concentrate. Purify the crude material by flash chromatography using a linear gradient of 100% hexanes to 40% EtOAc/hexanes to give (2-methoxy-5-trifluoromethoxy-phenyl)-methanol (6.86 g, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (m, 1H), 7.10 (dd, 1H, J=2.9, 8.8 Hz), 6.83 (d, 1H, J=8.8 Hz), 4.66 (d, 2H, J=6.4 Hz), 3.85 (s, 3H), 2.21 (t, 1H, J=6.4 Hz).

Aufarbeitung

  1. customcarefully quench with 1N HCl to pH 3
  2. concentrationConcentrate
  3. extractionextract the aqueous mixture with CH2Cl2 (3×100 mL)
  4. washCombine the organic phases and wash with saturated NaHCO3 (100 mL) and brine (100 mL)
  5. customDry the organic layer
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4896a6c2c8074929a1b7a454347ed2d5
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179804B2

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