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Water → 4-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butan-1-ol

HRID 1047488
Notes
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Reaction equation

HRID 1047488 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([CH3:26])[CH:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[F:15].[BH4-].[Li+].O.C(OCC)(=O)C>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([CH:6]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=2[F:15])[CH:5]([CH3:26])[CH2:4][CH2:3][OH:2])(=[O:17])=[O:18])=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 589501144-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butyric acid methyl ester

Product 1

HCID 589506574-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

4-(4-Chloro-benzenesulfonyl)-3-methyl-4-(2,3,6-trifluoro-phenyl)-butyric acid methyl ester (0.79 g, 1.88 mmol) was dissolved in 10 mL of THF and lithium borohydride (0.5 g, excess) was added. The reaction mixture was stirred at room temperature overnight. 50 mL of water and 50 mL of EtOAc were added. The organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was used in next step without further purification (0.71 g, 96%). 1H NMR (CDCl3 400 MHz) δ 7.61 (m, 2H), 7.36 (m, 2H), 7.06 (m, 1H), 6.82 (m, 0.5H), 6.60 (m, 0.5H), 4.79 (m, 0.5H), 4.56 (m, 0.5H), 3.85 (m, 1H), 3.68 (m, 1H), 3.12 (m, 1H), 2.39 (m, 0.5H), 1.95 (m, 0.5H), 1.57 (m, 0.5H), 1.46 (dd, J=4.4 and 5.9 Hz, 1.5H), 1.32 (m, 0.5H), 0.92 (dd, J=7.3 and 9.5 Hz, 1.5H).

Workup

  1. washThe organic layer was washed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was used in next step without further purification (0.71 g, 96%)

Sources & evidence

ORD record
ord-9ae5a6e824fd4ecba5eaa114a504dee0
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569521B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes