Water → Methyl 4-[4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy]butanoate

HRID 533490

Reaktionsgleichung

Reaktionsgleichung von HRID 533490
[CH:1]([C:3]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:5]([O:20][CH3:21])[CH:4]=1)=[O:2].[BH4-].[Na+].O.[K+].[Br-]>C1COCC1.CCCCCC.CCOC(C)=O>[OH:2][CH2:1][C:3]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:5]([O:20][CH3:21])[CH:4]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 253877Potassium BromideHCID 4311764Sodium borohydrideHCID 11033807Butanoic acid, 4-(4-formyl-2-methoxy-5-nitrophenoxy)-, methyl ester

Produkt 1

HCID 15334312Methyl 4-[4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy]butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel2×

Versuchsvorschrift

To a clear yellow solution of methyl 4-(4′-formyl-2′-methoxy-5′-nitrophenoxy) butanoate (5) (1 g, 3.36 mmol) in THF (10 cm3) was added, portion wise, sodium borohydride (128 mg, 3.36 mmol). The solution quickly changed appearance, becoming deep orange after about 5 mins. The mixture was stirred for a further 55 mins before water was added (25 cm3), the subsequent yellow mixture was extracted with ether (3×30 cm3) and the combined organic extracts were dried (MgSO4) and concentrated in vacuo providing a pale yellow solid. The solid, 6 was used without further purification (875 mg, 87.5%). A small amount of material (200 mg, 0.67 mmol) was purified via column chromatography (SiO2, hexane:EtOAc 2:1 v/v) so that complete characterisation data could be obtained. m.p. 100° C. [lit. (D. L. McMinn and M. M. Greenberg, Tetrahedron, 1996, 52, 3827.) m.p. 98-100° C.]. Found C, 52.2; H, 5.7; N, 4.7; C13H17NO7 requires C, 52.2; H, 5.7; N, 4.7%; Rf 0.24 (SiO2, hexane:EtOAc 2:1 v/v); νmax (KBr disc)/cm−1 3400-3100 (br), 3000-2800 (m), 1730 (s), 1280, 1220; δH (200 MHz, CDCl3) 2.20 (2H, q, J=7.3 Hz, CH2), 2.56 (2H, t, J 7.3 Hz, CH2), 2.61 (1H, br, OH), 3.70 (3H, s, OCH3), 3.98 (3H, s, OCH3), 4.13 (2H, t, J=7.3 Hz, CH2), 4.95 (2H, s, CH2), 7.15 (1H, s, H-3′), 7.71 (1H, s, H-6′) ppm; δC (100 MHz, CDCl3) 24.3 (CH2), 30.4 (CH2), 51.7 (OCH3), 56.4 (OCH3), 62.8 (CH2), 68.3 (CH2), 109.5 (CH), 111.2 (CH), 132.4, 139.6, 147.2, 154.3, 173.4 (COOCH3) ppm; m/z (FAB) 299 [(M+), 15%], 282 [(M-OH), 40%].

Aufarbeitung

  1. additionwas added (25 cm3)
  2. extractionthe subsequent yellow mixture was extracted with ether (3×30 cm3)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customproviding a pale yellow solid
  6. customThe solid, 6 was used without further purification (875 mg, 87.5%)
  7. customcould be obtained

Quellen und Nachweise

ORD-Eintrag
ord-7e57bbad69484b49ad89e3e6b8c2a131
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853270B2

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