tert-Butyldimethylsilyl chloride → HCID 15340541, compound

HRID 1684506Notes

Reaction equation

HRID 1684506 reaction equation
[CH2:1]([OH:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]#[CH:31].[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>C(Cl)(Cl)Cl.C(N(CC)CC)C.CN(C)C1C=CN=CC=1>[Si:33]([O:32][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]#[CH:31])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

6

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 15340540HCID 15340540, compound

Product 1

HCID 15340541HCID 15340541, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

9.6 g (0.0214 mol) of hentriacont-30-yn-1-ol of Example 10 were stirred vigorously in a mixture of 100 ml of chloroform and 4.4 ml of triethylamine for 1 h at room temperature. 3.5 g (0.0235 mol) of t-butyldimethylsilyl chloride were added, followed by a catalytic amount (spatula tipful) of 4-dimethylaminopyridine. The mixture was left to stand overnight at room temperature and half the solvent was stripped off. The remaining solution was chromatographed on a silica gel column (chloroform).

Workup

  1. waitThe mixture was left
  2. customThe remaining solution was chromatographed on a silica gel column (chloroform)

Sources & evidence

ORD record
ord-458d9ebe28a04046a11c48730a517d0f
Source dataset
uspto-grants-1997_06
Patent number
US05641767

Reaction notes

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