Methanol → 5-Bromo-2-methyl-2-phenylpentan-1-ol

HRID 239080

Reaktionsgleichung

Reaktionsgleichung von HRID 239080
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22](OCC)=[O:23].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][OH:23]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-olHCID 23431358Ethyl 5-bromo-2-methyl-2-phenyl-pentanoate

Produkt 1

HCID 113458925-Bromo-2-methyl-2-phenylpentan-1-olAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

According to the procedure given for the synthesis of 206e, 205b (23.70 g, 79.21 mmol) was reduced with LiBH4 (3.45 g, 158.4 mmol) and methanol (5.24 g, 163.5 mmol) in anhydrous CH2Cl2 (150 mL) to give 206b (20.0 g, 98%) as an oil. 1H NMR (CDCl3): δ 7.34-7.14 (m, 5 H), 3.60 (m, 1 H), 3.48 (m, 1 H), 3.29 (t, 2 H, J=6.0), 1.96-1.44 (m, 5 H), 1.32 (s, 3 H). 13C NMR (CDCl3): δ 144.25, 128.59, 126.71, 126.41, 72.44, 43.15, 37.06, 34.64, 27.58, 21.61. HRMS (LSIMS, nba): Calcd for C12H16Br (MH+-H2O): 239.0435, found: 239.0444.

Quellen und Nachweise

ORD-Eintrag
ord-4d171bc6f05a44ee8f0e1bd9010e9b23
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642653B2

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