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Boc-indole → tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

HRID 1821936
Notes
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Reaction equation

HRID 1821936 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH:19]([CH2:36]C([O-])=O)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1>CS(C)=O.[Na+].[Cl-]>[C:1]([O:5][C:6]([C:8]1[N:9]([CH2:36][CH:19]([O:7][C:6](=[O:5])[CH3:8])[CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11458614Boc-indoleHCID 86606004HCID 86606004, compound

Product 1

HCID 11526497tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

0.325 g (1.50 mmol) tert-butylindole-2-carboxylate is dissolved in 15 ml absolute DMSO, mixed with 0.184 g (1.64 mmol) potassium-tert-butylate and stirred at 110° C. for 15 min. A solution of 0.576 g (1.50 mmol) [1-bromo-3-(4-octylphenoxy)propan-2-yl]acetate in 15 ml absolute DMSO is added drop-wise. Following 30 minutes of heating at 110° C. and subsequent cooling, hydrolysis is carried out in saturated NaCl solution. Four extractions with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 99:1) and yields the product as a colorless oil.

Workup

  1. waitFollowing 30 minutes
  2. temperatureof heating at 110° C.
  3. customsubsequent cooling, hydrolysis
  4. extractionFour extractions
  5. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  6. customon the rotary evaporator, three
  7. washwash steps with saturated NaCl solution
  8. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  9. customleave as a crude product a yellow oil which
  10. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 99:1)

Sources & evidence

ORD record
ord-5f644bd9e7ff4654953bc9d2d697a932
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608633B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes