1-Bromohexadecane → HCID 19890449, compound

HRID 620656Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:11][CH3:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:29]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:11][CH3:12])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

6-Hydroxy-5-methoxyindole (2 g; 0.0123 mole) dissolved in 10 ml of dimethylformamide (DMF) is introduced dropwise in the course of 20 minutes into a mixture of 1-bromohexadecane (4.5 g; 0.0148 mole) and potassium carbonate (1.87 g; 0.0135 mole) in 45 ml of DMF at 70° C. and under nitrogen. The reaction mixture is stirred under nitrogen at 80° C. for 3 and a half hours. The blackish mixture is poured into ice-cold water with stirring and the brownish solid formed is immediately filtered off and washed with water. It is taken up in dichloromethane and dried over sodium sulphate. After chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane, the derivative 26 is obtained (1.66 g; 35% yield).

Workup

additionThe blackish mixture is poured into ice-cold water
stirringwith stirring
customthe brownish solid formed
filtrationis immediately filtered off
washwashed with water
dry with materialdried over sodium sulphate
customAfter chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane
customthe derivative 26 is obtained (1.66 g; 35% yield)

Sources & evidence

ORD record: ord-f35504cd59cf4b16971b3393f9c0896c
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822375

Reaction notes

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