Silane, tris(1-methylethyl)- → 2-(3-Mercaptopropyl)pentanedioic acid

HRID 1976719Notes

Reaction equation

HRID 1976719 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:8][CH2:9][CH2:10][CH2:11][CH:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])C=CC=CC=1.C([SiH](C(C)C)C(C)C)(C)C>C(Cl)Cl>[SH:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 138754Silane, tris(1-methylethyl)-HCID 111341182-(3-tritylsulfanylpropyl)pentanedioic acid

Product 1

HCID 101981712-(3-Mercaptopropyl)pentanedioic acidYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.46 mmol of 6-[(triphenylmethyl)thio]-1,3-hexanedicarboxylic acid (IV) (1.1 g) with 5 mmol triisopropylsilane (0.79 g) was dissolved in a mixture of 3 ml CH2Cl2/3 ml trifluoroacetic acid and left to stand at room temperature for 1 hour. The mixture was then evaporated to dryness and washed 3× with hexane. The remaining oily residue was dissolved in water, filtered and lyophilized to yield 0.35 g of 2-(3-sulfanylpropyl)pentanedioic acid (V) (76%), 13C-NMR (MeOH) δ 25.2(t), 28.8(t), 32.4(t), 33.0(t), 33.2(t), 45.9(d), 177.2(s), 179.6(s).

Workup

  1. waitleft
  2. customThe mixture was then evaporated to dryness
  3. washwashed 3× with hexane
  4. dissolutionThe remaining oily residue was dissolved in water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9ee42fa33d1b4ad3863b5a66b84fddc9
Source dataset
uspto-grants-2001_05
Patent number
US06228888B1

Reaction notes

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