Reaktion #76387

Reaktionsgleichung

6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid

6-Benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid

(R)-1-methylheptyl-1

(R)-2-octanol

DMAP

→

6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (1S)-1-methylheptyl ester

Ausbeute 53.0%

6-Benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester

Ausbeute 53.0%

Lösungsmittel

THF

DIC

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with water
2. 2
   Extraktionextracted with ethyl acetate:hexane(1:1)
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by chromatography on silica gel (3% EtOAc/hexanes)

Vorschrift

To a solution of 6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (31) (1 equi.), (R)-1-methylheptyl-1-ol (13) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (3% EtOAc/hexanes) gave 6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (1S)-1-methylheptyl ester (36) as a colorless oil (53%).

Quelle