Sodium Carbonate → HCID 20481704, compound

HRID 1648736Notes

Reaction equation

HRID 1648736 reaction equation
Br[CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:22][C:23]([CH3:33])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:25][NH2:26].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[OH:22][C:23]([CH3:33])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:25][NH:26][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 20481699HCID 20481699, compoundHCID 20481702HCID 20481702, compound

Product 1

HCID 20481704HCID 20481704, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-bromo-9-tetrahydropyranyloxy-nonanoate (2.5 g) and 3-hydroxy-3-methylnonylamine (2.2 g) were refluxed together in dry ethanol (50 ml) containing sodium carbonate (726 mg) overnight. The ethanol was evaporated in vacuo and the residue was partitioned between ether and brine. The ether solution was washed with brine, dried and evaporated in vacuo. The resulting yellow gum was chromatographed on silica gel (100 g) using chloroform as eluant to give ethyl 2-(3'-hydroxy-3'-methyl-n-nonyl)amino-9-tetrahydropyranyloxy-nonanoate (1.27 g) as a colourless gum.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. customthe residue was partitioned between ether and brine
  3. washThe ether solution was washed with brine
  4. customdried
  5. customevaporated in vacuo
  6. customThe resulting yellow gum was chromatographed on silica gel (100 g)

Sources & evidence

ORD record
ord-160a855a1ba84768b1a6a0d8e8e55a16
Source dataset
uspto-grants-1983_11
Patent number
US04413002

Reaction notes

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