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Hydrochloric Acid → trityloxy-acetic Acid Ethyl Ester

HRID 1714491
Notes
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Reaction equation

HRID 1714491 reaction equation
[C:1](Cl)([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.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:22][OH:23].N1C=CC=CC=1.Cl>C(Cl)CCl>[CH2:26]([O:25][C:21](=[O:24])[CH2:22][O:23][C: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)[CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6456Trityl chlorideHCID 12184Ethyl Glycolate

Product 1

HCID 12230788trityloxy-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

Trityl chloride (279 g, 1.0 mol) was dissolved in EDC (680 ml, 5 ml/g with respect to ethyl glycolate), and ethyl glycolate (135 g, 1.3 mol) was added to the mixture. Pyridine (99 g, 1.25 mol) was added thereto, and the mixture was stirred for 19 hours at 40° C. After completion of the reaction was confirmed by HPLC, 0.5 N aqueous hydrochloric acid solution (270 ml, 2 ml/g with respect to ethyl glycolate) was added to make the reaction solution a two-phase solution, which was then extracted. After the extraction was performed once again, EDC was distilled under reduced pressure. In order to obtain the compound of formula (8) as a solid form, hexane (680 ml) was added to the concentrated compound, the temperature was lowered to 0° C., and the mixture was stirred for about 3 hours and filtered.

Workup

  1. additionwas added
  2. extractionwas then extracted
  3. extractionAfter the extraction
  4. distillationEDC was distilled under reduced pressure

Sources & evidence

ORD record
ord-9f0efe9728874fb78787a3eea89ecbbb
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795463B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes