Dimethylformamide → HCID 20282927, compound

HRID 2295425Notes

Reaction equation

HRID 2295425 reaction equation
[C:1]([C:4]1[C:31](O)=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([O:25]CC)=[O:24])[CH:17]=[CH:16]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:39](Br)[CH:40]=C.CN(C)[CH:45]=[O:46]>O>[C:1]([C:4]1[C:31]([O:46][CH2:45][CH:39]=[CH2:40])=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([OH:25])=[O:24])[CH:17]=[CH:16]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 20282973HCID 20282973, compound

Product 1

HCID 20282927HCID 20282927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 6-[5-(2-acetyl-3-hydroxyphenoxy)pentyloxy]naphthalene-2-carboxylate (1.85 g), potassium carbonate (0.59 g) and allyl bromide (0.74 ml) were stirred in dry dimethyl formamide (40 ml) for 20 hr. The mixture was diluted with water and extracted with ethyl acetate, which was washed with water, dried and evaporated to yield the ethyl ester of the sub-title compound (2.2 g) as a pale yellow solid. The ester (0.65 g) was hydrolysed by the method of Example 2f to give the title acid (0.36 g), mp 157°-157.5°.

Workup

  1. extractionextracted with ethyl acetate, which
  2. washwas washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b656e2fdb7c34f87843b9ad437a591ad
Source dataset
uspto-grants-1984_01
Patent number
US04424231

Reaction notes

Loading…