Pyridine → Benzene, 1,1',1''-[(3-butynyloxy)methylidyne]tris-

HRID 128199Notes

Reaction equation

HRID 128199 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([OH:25])[CH2:22][C:23]#[CH:24].N1C=CC=CC=1>ClCCl>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:25][CH2:21][CH2:22][C:23]#[CH:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 135663-Butyn-1-OL

Product 1

HCID 11197747Benzene, 1,1',1''-[(3-butynyloxy)methylidyne]tris-Yield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylmethyl chloride (122 g, 0.44 mol) is added to a solution of but-3-yne-1-ol (25 g, 0.36 mol) in dichloromethane (400 ml) containing pyridine (50 ml) and stirred overnight at room temperature. The reaction mixture is filtered and washed with cold dilute hydrochloric acid, aqueous sodium bicarbonate and water. The dried solution is concentrated to a solid which is crystallized from ether-petroleum ether to give 4-triphenylmethyloxybut-1-yne (60 g), m.p. 97°-99° (ether-petroleum ether).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with cold dilute hydrochloric acid, aqueous sodium bicarbonate and water
  3. concentrationThe dried solution is concentrated to a solid which
  4. customis crystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-a7c288e18a244ce59b22440ee65e797d
Source dataset
uspto-grants-1981_03
Patent number
US04259324

Reaction notes

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