1-Hydroxyethyl radical → HCID 86738260, compound

HRID 1157047Notes

Reaction equation

HRID 1157047 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:22][CH3:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1.[O-][CH2:26][CH3:27]>C(O)C1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20][CH2:21][C:27]2[CH:26]=[CH:4][CH:3]=[CH:2][CH:14]=2)=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:22][CH3:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1

Participants

5

Reactant 2

HCID 1194401-Hydroxyethyl radicalHCID 12806942methyl [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate

Product 1

HCID 86738260HCID 86738260, compound

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate (Example 20, Step C) (5.8 g., 0.016 mole) is dissolved in a mixture of dry benzyl alcohol (50 ml) and methylene chloride (40 ml.) containing amberlite IRA 400 (ethoxide) (5-6 g.). The mixture is stirred magnetically at reflux for four hours and then filtered. The filtrate is concentrated in vacuo to give a yellow solid (5.3 g.) which upon trituration with ethanol and washing with ether yields the product.

Workup

  1. temperatureat reflux for four hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a yellow solid (5.3 g.) which upon trituration with ethanol
  5. washwashing with ether
  6. customyields the product

Sources & evidence

ORD record
ord-38617589bc7a4a6ead151d55543f1676
Source dataset
uspto-grants-1982_06
Patent number
US04337354

Reaction notes

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