Propargyl alcohol → HCID 53775572, compound

HRID 1284431Notes

Reaction equation

HRID 1284431 reaction equation
[CH2:1]([P:3]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=[O:5])[OH:4])[CH3:2].S(Cl)(Cl)=O.[CH2:31](O)[C:32]#[CH:33].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([P:3]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=[O:4])[O:5][CH2:33][C:32]#[CH:31])[CH3:2]

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 15589803P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinic acid

Product 1

HCID 53775572HCID 53775572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To P-ethyl-2-nitro-5-(2-chloro-4-trifluoro-methylphenoxy)phenylphosphinic acid chloride, prepared from P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)-phenylphosphinic acid (500 mg, 1.22 mmol) and thionyl chloride (3 ml) by the procedure of Example 25, in methylene chloride (3 ml) is added propargyl alcohol (3 ml) and triethyl amine (0.2 ml). The mixture is stirred at RT for 4 hours, after which the reaction is taken up in methylene chloride, washed, dried and evaporated. The crude product is purified by prep. TLC to give propargyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate, m/s 447 (M+).

Workup

  1. washwashed
  2. customdried
  3. customevaporated
  4. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-d2720e9344cc45e680daf8c622bc9738
Source dataset
uspto-grants-1986_01
Patent number
US04563310

Reaction notes

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