2-(Dimethylamino)ethanol → HCID 53923166, compound

HRID 2225707Notes

Reaction equation

HRID 2225707 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]O>ClCCl>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:23][C:22](=[O:24])[C:21](=[O:25])[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 19004267HCID 19004267, compound

Product 1

HCID 53923166HCID 53923166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The acid chloride, prepared from 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alphaoxobenzeneacetic acid (0.5 g) as described in Example 6, was dissolved in dichloromethane (10 mL) and added dropwise to a stirred, cold (<-50° C.) mixture of 2-(dimethylamino)ethanol (0.178 g) in dichloromethane (10 mL). The cooling bath was removed and the mixture stirred for 1 hour at room temperature. The mixture was diluted with dichloromethane and washed once with saturated aqueous sodium bicarbonate, once with water, and the organic solution was dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from diethyl ether-hexane provided pure 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid 2-(dimethylamino)ethyl ester as a colorless solid, mp 93°-94° C.

Workup

  1. customThe cooling bath was removed
  2. additionThe mixture was diluted with dichloromethane
  3. washwashed once with saturated aqueous sodium bicarbonate, once with water
  4. dry with materialthe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customCrystallization from diethyl ether-hexane provided pure 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid 2-(dimethylamino)ethyl ester as a colorless solid, mp 93°-94° C.

Sources & evidence

ORD record
ord-d3b91e4f16c441a4aac0ff0ca67f80f2
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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