2-Bromobenzyl alcohol → 8-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

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Reaktionsgleichung

Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Li]CCCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1>C1COCC1>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:21]1([OH:24])[CH2:22][CH2:23][C:18]2([O:25][CH2:15][CH2:16][O:17]2)[CH2:19][CH2:20]1

Komponenten

Reaktionsbedingungen

Temperatur: -4 °C

Versuchsvorschrift

To a solution of 2-bromobenzyl alcohol (3.0 g, 16 mmol) in THF (40 mL) cooled at −78° C. was added a 2.5 M solution of n-BuLi in hexanes (14.1 mL). The mixture was stirred at −4° C. for 1 hour and cooled back to −78° C. To it was added a solution of 1,4-cyclohexanedione mono-ethylene ketal (2.5 g, 16 mmol) in TIE (10 mL) over 15 minutes. Stirring was continued at −78° C. for 30 minutes and at −4° C. for 1 hour. The reaction was quenched by addition of a solution of NH4Cl in water. The resulting solution was extracted with EtOAc three times. The combined extract was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 5% MeOH/CH2Cl2 provided the title compound. MS calculated (M+H)+265. Found 287 (M+Na)+.

Aufarbeitung

temperaturecooled back to −78° C
stirringStirring
waitwas continued at −78° C. for 30 minutes and at −4° C. for 1 hour
customThe reaction was quenched by addition of a solution of NH4Cl in water
extractionThe resulting solution was extracted with EtOAc three times
extractionThe combined extract
washwas washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customPurification on silica gel eluting with 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag: ord-8d5bc23c37034981801e7e8145bb2ea5
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08362003B2

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