Tetrahydrofuran → Tert-butyl 4-[2-hydroxy-1-(hydroxymethyl)ethyl]benzoate

HRID 1013538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013538
[BH4-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:21](OC)=[O:22])[C:17](OC)=[O:18])=[CH:12][CH:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C1COCC1>CO>[OH:18][CH2:17][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([C:8]([O:7][C:3]([CH3:4])([CH3:6])[CH3:5])=[O:9])=[CH:11][CH:12]=1)[CH2:21][OH:22]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57541233Dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate

Produkt 1

HCID 57925849Tert-butyl 4-[2-hydroxy-1-(hydroxymethyl)ethyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of NaBH4 (1.23 g, 32.4 mmol) in MeOH (20 ml) was added a solution of dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate (2.00 g, 6.49 mmol) in 3:2 MeOH:THF (18 mL). The reaction was stirred at room temperature for 2 h. It was then quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded tert-butyl 4-[2-hydroxy-1-(hydroxymethyl)ethyl]benzoate as a colorless solid. 1H NMR (CDCl3, 600 MHz) δ 7.93 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.2 Hz, 2H), 3.99 (ddd, J=10.8, 7.4, 5.1 Hz, 2H), 3.93 (dt, J=10.7, 5.2 Hz, 2H), 3.13 (tt, J=7.6, 5.5 Hz, 1H), 2.14 (t, J=5.3 Hz, 2H), 1.56 (s, 9H). MS: cal'd 275 (MH+), exp 275 (M)H+).

Aufarbeitung

  1. customIt was then quenched with saturated NH4Cl
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e21e9845a79043c4afcae81968860e8c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981874B2

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