Methyl bromoacetate → HCID 54348637, compound

HRID 1901778Notes

Reaction equation

HRID 1901778 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=2)[NH:7][C:6]=1[CH2:20]C.C1(OC2C=C3C(=CC=2)NC(CC)=C3)CCCC1.C([Li])CCC.BrCC(OC)=O>CCCCCC.CCOCC.[Cl-].[Cl-].[Zn+2]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=2)[NH:7][C:6]=1[CH3:20]

Participants

8

Reactant 4

HCID 60984Methyl bromoacetateHCID 23368773HCID 23368773, compoundHCID 53843375HCID 53843375, compoundHCID 178418339Butyllithium

Product 1

HCID 54348637HCID 54348637, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

5-Cyclopentoxy-2-ethyl-1H-indole-3-acetic acid methyl ester. As in Example 1, Part E, 2.33 g (0.0102 mol) of 5-cyclopentoxy-2-ethyl-1H-indole was treated with 6.4 mL (0.0102 mol) of a 1.6M solution of n-butyl lithum in hexane, 10.2 mL (0.0102 mol) of a 1M solution of ZnCl2 in ether, and 0.97 mL (0.0102 mol) of methyl 2-bromoacetate to give after chromatography on silica (5% EtOAc/toluene) 1.8 g (59%) of 5-cyclopentoxy-2-methyl-1H-indole-3-acetic acid methyl ester as an oil.

Sources & evidence

ORD record
ord-4a4ab3cb15864d949dd65e989bcf6940
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

Loading…