Benzyl Bromide → 5-Ethyl-4-benzyloxy-3-methylbenzofuran-2-carboxylic acid ethyl ester

HRID 29324Notes

Reaction equation

HRID 29324 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:13])=[C:8]([CH2:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:17]([O:16][C:14]([C:3]1[O:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[C:7]([O:13][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]=2[C:2]=1[CH3:1])=[O:15])[CH3:18]

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 68711669Ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate

Product 1

HCID 687140205-Ethyl-4-benzyloxy-3-methylbenzofuran-2-carboxylic acid ethyl esterYield 99.8%

Procedure

According to the procedure of Example 86, Step 3, 0.250 g (1.01 mmol) of 3-methyl-4-hydroxy-5-ethylbenzofuran carboxylic acid ethyl ester (Example 86, Step 2) and 0.599 mL (5.04 mmol) of benzyl bromide gave 0.341 g of 5-ethyl-4-benzyloxy-3-methylbenzofuran-2-carboxylic acid ethyl ester after chromatography on silica gel eluting with ethyl acetate/hexanes (1:20).

Sources & evidence

ORD record
ord-c1ba28bdda7f43389a3dc1e9a2fbfd7d
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…