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Tetrahydrofuran → 2-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyran

HRID 582606
Notes
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Reaction equation

HRID 582606 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([C:22]([F:25])([F:24])[F:23])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)([O-])O.[Na+]>O>[C:1]1([CH2:7][O:8][CH:9]([C:22]([F:25])([F:23])[F:24])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([NH:21][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 153456682-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-amino-3,4-dihydro-2H-1-benzopyran

Product 1

HCID 110043812-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3.6 g (10 mmol) of 2-(2-phenylmethoxy-3,3,3-trifluoropropyl)-6-amino-3,4-dihydro-2H-1-benzopyran in 34 ml of a 9/1 mixture of tetrahydrofuran and water is reacted for 20 min with 1.1 ml (11 mmol) of ethyl chloroformate and 1.3 g (15 mmol) of sodium hydrogencarbonate. The mixture is then diluted with water and the product is extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. By chromatography of the residue on a silica column using a 20/80 mixture of cyclohexane and dichloromethane, 4.2 g of product are obtained.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additiona 20/80 mixture of cyclohexane and dichloromethane, 4.2 g of product
  5. customare obtained

Sources & evidence

ORD record
ord-8e04965a2163400db93cf7ad81737364
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05925662

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes