Myristyl bromide → HCID 53728312, compound

HRID 1492847Notes

Reaction equation

HRID 1492847 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([OH:29])[CH:5]=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:5]=[C:6]([O:29][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH3:32])[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 54194410HCID 54194410, compound

Product 1

HCID 53728312HCID 53728312, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (2.45 mmol) of 3-hydroxy-5-[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester, 0.73 ml (2.69 mmol) of 1-bromotetradecane and 0.7 g (4.9 mmol) of potassium carbonate in 20 ml of anhydrous DMF was stirred and heated at 80° for 22 hours. The usual workup followed by chromatography on 30 g of silica gel using 10% ethyl acetate-hexane, trituration of the combined pure fractions with methanol and filtration gave 1.37 g (93% yield, mp 69°-70°) of 3-[3-[4-(phenylmethoxy)phenoxy]propoxy]-5-(tetradecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureheated at 80° for 22 hours
  2. filtrationThe usual workup followed by chromatography on 30 g of silica gel using 10% ethyl acetate-hexane, trituration of the combined pure fractions with methanol and filtration

Sources & evidence

ORD record
ord-1801fda759cc48988d706e6eaada7515
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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