Trityl chloride → HCID 15085407, compound

HRID 2221129Notes

Reaction equation

HRID 2221129 reaction equation
[SH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C1COCC1>CO.C(OCC)(=O)C.C(O)C>[C:14]([S:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10465720Ethanol, 2-[2-[2-(2-mercaptoethoxy)ethoxy]ethoxy]-

Product 1

HCID 15085407HCID 15085407, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

To 2-{2-[2-(2-mercapto-ethoxy)-ethoxy]-ethoxy}-ethanol (310 mg, 1.47 mmol) and trityl chloride (452 mg, 1.62 mmol, 1.1 eq.) in a round bottomed flask was added simultaneously triethylamine (2.1 ml, 10 eq.) and THF (25 ml) under argon. The initial red colour faded upon stirring at ambient temperature for 1 hour. The reaction was monitored by TLC, ethyl acetate/ethanol (1:1) and was completed after 6 hours. Thereafter methanol (6 ml) was added to consume excess trityl chloride and the mixture stirred for 5 minutes before evaporation of the solvents. The residue was purified by flash chromatography using 100% ethyl acetate to afford the product (550 mg, 83%) as a colourless oil.

Workup

  1. waitwas completed after 6 hours
  2. customto consume excess trityl chloride
  3. stirringthe mixture stirred for 5 minutes before evaporation of the solvents
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ca9e807440e34433a3ff48aa6802a408
Source dataset
uspto-grants-2008_05
Patent number
US07368474B2

Reaction notes

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