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Ammonium Chloride → 1-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol

HRID 916047
Notes
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Reaction equation

HRID 916047 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[Li+].CC([N-]C(C)C)C.[O:19]1[C:23]2[C:24]([C:28]([CH3:33])([CH3:32])[CH2:29][CH:30]=[O:31])=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20]1.[Cl-].[NH4+]>C1COCC1.CN1C(=O)N(C)CCC1.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH:30]([OH:31])[CH2:29][C:28]([C:24]1[C:23]2[O:19][CH2:20][CH2:21][C:22]=2[CH:27]=[CH:26][CH:25]=1)([CH3:33])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 888943-Chloro-p-toluonitrileHCID 2724682Lithium diisopropylamideHCID 589599393-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanal

Product 1

HCID 589600171-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanolYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 22565281tetrahydrofuran 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinoneSolvent

Procedure

A solution of 2-chloro-4-cyanotoluene (606 mg) in THF/DMPU (1:1, 8 mL) was treated dropwise with LDA (1.8 M in heptane/ethylbenzene/THF, 2.44 mL) at −78° C. After 30 minutes, 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanal (400 mg) was added in THF (1 mL) and the mixture was subsequently warmed to room temperature. After 1 hour, 5 mL of saturated ammonium chloride solution was added. The organic phase was separated and the aqueous layer was extracted with 20 mL of ethyl acetate. The combined organic phases were washed with three 10 mL portions of water and dried over magnesium sulfate. The solvent was removed. Flash chromatography (hexanes-EtOAc (gradient from 10:1 to 5:1)) of the residue yielded 460 mg (66%) of 1-(2-chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol as a colorless oil.

Workup

  1. waitAfter 1 hour
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted with 20 mL of ethyl acetate
  4. washThe combined organic phases were washed with three 10 mL portions of water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-a21f9c193894482aaa117c6a31fdbcdb
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07268152B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes