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Water → HCID 54249207, compound

HRID 275546
Notes
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Reaction equation

HRID 275546 reaction equation
[C:1]([N:20]1[CH:24]=[N:23][C:22](I)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([OH:29])[C:27]#[CH:28].C(N(CC)CC)C.O>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:29][CH2:26][C:27]#[C:28][C:22]1[N:23]=[CH:24][N:20]([C:1]([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)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 542286423-Iodo-1-trityl-1H-1,2,4-triazole

Product 1

HCID 54249207HCID 54249207, compound

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-trityl-3-iodo-1,2,4-triazole (26.24 g, prepared as described in Example 5), propargyl alcohol (3.56 ml) and triethylamine (40 ml) in dry N,N-dimethylformamide (750 ml) was treated successively with tetrakis(triphenylphosphine)palladium (2.77 g) and cuprous iodide (1.0 g). It was stirred for four hours at room temperature under nitrogen and allowed to stand overnight but the reaction had not proceeded to completion. Stirring was continued for a further four periods of seven hours, then the mixture was poured into water (11) and extracted with chloroform (5×250 ml). The extracts were dried over magnesium sulphate, evaporated under reduced pressure and chromatographed on silica, using ethyl acetate-hexane (4:1) as eluant. Trituration with ether gave 1-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)prop-2-yne (12.20 g). Recrystallisation from chloroform gave material m.p. 211° C. NMR (CDCl3): δ 4.45(2H,s), 7.1-7.3(15H,m), 7.95(1H,s). 13C NMR provided confirmation. M/S: M+ 365.

Workup

  1. waitto stand overnight
  2. stirringStirring
  3. customwas continued for a further four periods of seven hours
  4. extractionextracted with chloroform (5×250 ml)
  5. dry with materialThe extracts were dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customchromatographed on silica

Sources & evidence

ORD record
ord-c9cd05d1f9e0453ba25d84561c351980
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05393732

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes