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Phenylacetylene → Benzyl 2-benzyloxy-4-phenylethynyl-benzoate

HRID 322935
Notes
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Reaction equation

HRID 322935 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23](I)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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.[Cu]Br.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([C:33]#[C:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 10599389Benzyl 2-benzyloxy-4-iodobenzoate

Product 1

HCID 10598112Benzyl 2-benzyloxy-4-phenylethynyl-benzoateYield 27.9%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 178418397HCID 178418397, compound
Catalyst
HCID 8471TriethylamineSolvent

Procedure

Benzyl 2-benzyloxy-4-iodobenzoate (7.6 g) is added to triethylamine (120 mL) followed by phenylacetylene (2.94 g) then tetrakis(triphenylphosphine)palladium(0) (0.664 g) and copper (I) bromide (0.248 g). The resulting mixture is stirred at room temperature for 3 hours. The triethylamine is distilled off and the residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution. The organic phase is dried over magnesium sulphate and evaporated. The residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give benzyl 2-benzyloxy-4-phenylethynyl-benzoate (2 g) as a cream solid, m.p. 98-100° C.

Workup

  1. distillationThe triethylamine is distilled off
  2. customthe residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v)
  6. customevaporated

Sources & evidence

ORD record
ord-01ddd84156a7448b9f22bb951797c3bf
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes