Hydrochloric Acid → 1-[(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea

HRID 367310Notes

Reaction equation

HRID 367310 reaction equation
C([O:4][C:5]1[C:6]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][C:8]2[O:12][C:11]([CH2:14][NH:15][C:16]([NH2:18])=[S:17])([CH3:13])[CH2:10][C:9]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=O)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[C:20]([C:19]1[C:9]2[CH2:10][C:11]([CH2:14][NH:15][C:16]([NH2:18])=[S:17])([CH3:13])[O:12][C:8]=2[CH:7]=[C:6]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]=1[OH:4])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 232880401-[(5-Acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea

Product 1

HCID 154857291-[(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thioureaYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, 1.0 g of 1-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea was dissolved in 30 ml of toluene. To the solution was added 10.2 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 1 hour. After reaction, the mixture was combined with a saturated aqueous ammonium chloride solution and 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with n-hexane containing 33% ethyl acetate to give 0.89 g of 1-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]thiourea as a white crystal (yield 100%).

Workup

  1. customAfter reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography
  7. washeluting with n-hexane containing 33% ethyl acetate

Sources & evidence

ORD record
ord-3e2c9dcfa8b84de39e383c05f0ed4b0e
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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