Dichloromethane → HCID 59550251, compound

HRID 885769Notes

Reaction equation

HRID 885769 reaction equation
[OH:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]#[N:5].C(Cl)Cl.C(N(CC)CC)C.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>O>[CH3:27][Si:28]([CH3:30])([CH3:29])[O:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]#[N:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 15884599HCID 15884599, compound

Product 1

HCID 59550251HCID 59550251, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5 g of (R)-3-hydroxy-tetradecanenitrile and 35 ml of methylene chloride were placed in a reactor and stirred. The mixture was cooled to 0° C., and 3.87 ml of triethylamine was added thereto, to which 3.38 ml of trimethylsilyl chloride was added over about 30 minutes, and stirred for about 1 hour. Subsequently, the resulting mixture was slowly heated to room temperature and stirred for about 1 hour, 50 ml of water was added thereto, and stirred vigorously for 5 minutes. The aqueous layer was removed. The organic layer was combined with 50 ml of water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, to give 6.66 g of the title compound (yield: 100%) as an oil.

Workup

  1. stirringstirred for about 1 hour
  2. temperatureSubsequently, the resulting mixture was slowly heated to room temperature
  3. stirringstirred for about 1 hour
  4. stirringstirred vigorously for 5 minutes
  5. customThe aqueous layer was removed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-5973da13f68d46a4877f99d4b8d802a6
Source dataset
uspto-grants-2012_08
Patent number
US08242288B2

Reaction notes

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