Thionyl Chloride → HCID 131721091, compound

HRID 343758Notes

Reaction equation

HRID 343758 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[C:21]([O:25][C:26](=[O:38])[CH2:27][CH2:28][CH2:29][S:30][C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl.C1COCC1.CCOCC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH3:16])([CH3:15])[C:12]([O:14][C:34]2[CH:33]=[CH:32][C:31]([S:30][CH2:29][CH2:28][CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:38])=[CH:36][CH:35]=2)=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 81671922-(4-tert-butylphenyl)-2-methylpropanoic acidHCID 18781485HCID 18781485, compound

Product 1

HCID 131721091HCID 131721091, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-tert-butylphenylisobutyric acid (2.00 g, 0.0091 mol) and thionyl chloride (1.62 g, 0.0136 mol) in 16 ml of CH2Cl2 was allowed to stir overnight under Argon. The volatiles were removed under vacuum and the resulting solid was dissolved into THF (15 mL) and a solution of tert-butyl-4-(4'-hydroxyphenyl)mercaptobutyrate (2.44 g, 0.0091 mol), TEA (2.5 mL) in THF (15 mL) was added dropwise over 10 min. The mixture was stirred for 3 days, diluted with Et2O and extracted with 5% NaHCO3. The organics were washed with H2O, brine and dried (MgSO4). After evaporization the colored oil was separated (HPLC, silica gel 70:30 CH2Cl2 /hexane to CH2Cl2 linear graduent) to give the desired product as an oil (2.20 g, 51.5%). 1H NMR (CDCl3) δ 1.33 (s, 9H), 1.43 (s, 9H), 1.70 (s, 6H), 1.88 (tt, J=7.2 Hz, 2 H), 2.35 (t, J=7.2 Hz, 2H), 2.90 (t, J=7.2, 2H), 6.92 (d, J=8.6 Hz, 2H), 7.32 (d, J=8.6 Hz, 2H), 7.34-7.40 (m, 4H). 13C NMR (CDCl3) δ0 24.50, 26.42, 28.08, 31.31, 33.70, 34.11, 34.39, 46.40, 80.40, 121.92, 125.23, 125.46, 130.82, 133.03, 140.86, 149.58, 149.69, 172.21, 175.34.

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe resulting solid was dissolved into THF (15 mL)
  3. stirringThe mixture was stirred for 3 days
  4. extractionextracted with 5% NaHCO3
  5. washThe organics were washed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. customAfter evaporization the colored oil was separated (HPLC, silica gel 70:30 CH2Cl2 /hexane to CH2Cl2 linear graduent)

Sources & evidence

ORD record
ord-dbb66d2f3d11451abe0cbca99fbeeedc
Source dataset
uspto-grants-1999_01
Patent number
US05863899

Reaction notes

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