Triethylsilane → 11-(p-Tolyloxy)undecyl 3-mercaptopropioate

HRID 444612Notes

Reaction equation

HRID 444612 reaction equation
C([S:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)=[O:24])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[SH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][CH:43]=1)=[O:24]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 6754204611-(p-Tolyloxy)undecyl 3-(tritylthio)propioate

Product 1

HCID 8664555211-(p-Tolyloxy)undecyl 3-mercaptopropioate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The compound 17 (1.11 g) was weighed and poured into a 100-ml round-bottomed flask, and 10 ml of trifluoroacetic acid was added and stirred, to obtain an orange-colored homogenous solution. After 0.9 ml of triethylsilane was added to generate a white-colored precipitate, the supernatant solution (transparent) was distilled away under reduced pressure. The solid obtained was purified by chromatography, and 0.6 g of the compound e, which was a white solid, was obtained.

Workup

  1. additionpoured into a 100-ml round-bottomed flask
  2. customto obtain an orange-colored homogenous solution
  3. distillationthe supernatant solution (transparent) was distilled away under reduced pressure
  4. customThe solid obtained
  5. customwas purified by chromatography, and 0.6 g of the compound e, which
  6. customwas obtained

Sources & evidence

ORD record
ord-cf7d57de8ab74fdab78d8d5c544b7a27
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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