Tetrahydrofuran → HCID 10364634, compound

HRID 265410Notes

Reaction equation

HRID 265410 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1.O1CCCC1>CN(C)C1C=CN=CC=1.CCCCCC>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9](=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:26]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8400BenzoinHCID 10868DicyclohexylcarbodiimideHCID 5482758-Bromooctanoic acid

Product 1

HCID 10364634HCID 10364634, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

A mixture of benzoin (26.15 g), 8-bromooctanoic acid (25.0 g), 4-dimethylaminopyridine (1.35 g), 1,3-dicyclo-hexylcarbodiimide (25.4 g) and dry tetrahydrofuran (350 ml) was stirred under nitrogen at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane (350 ml), washed with 5% aqueous hydrochloric acid (3×175 ml), saturated sodium hydrogen carbonate solution (2×200 ml), saturated sodium chloride solution (220 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chro-matography on silica gel eluted with a hexane: dichloromethane gradient gave a yellow oil. This oil was stirred in hexane to give 2-oxo-1,2- diphenyl-ethyl 8-bromooctanoate (27.1 g, 52.7%) as a pale yellow solid m.p. 60°-61° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (350 ml)
  4. washwashed with 5% aqueous hydrochloric acid (3×175 ml), saturated sodium hydrogen carbonate solution (2×200 ml), saturated sodium chloride solution (220 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated to dryness in vacuo
  7. washColumn chro-matography on silica gel eluted with a hexane
  8. customdichloromethane gradient gave a yellow oil

Sources & evidence

ORD record
ord-2fc445d77a3e414ab5a4953c28ae85f1
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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