Pyridine → Decyl chloroformate

HRID 530488Notes

Reaction equation

HRID 530488 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[C:19]12([OH:29])CC3CC(C[CH:21](C3)[CH2:20]1)C2.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:2]([Cl:1])(=[O:4])[O:29][CH2:19][CH2:20][CH2:21][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:30][CH3:36]

Participants

5

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 641521-AdamantanolHCID 94429Triphosgene

Product 1

HCID 108727Decyl chloroformateYield 88%

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, triphosgene (9.75 g, 32.8 mmol) was dissolved in toluene (140 mL) under argon atmosphere. After cooling to 0° C., pyridine (8.5 mL, 105 mmol) was added dropwise during 1 h and the resulting suspension stirred for further 1 h at 0° C. 1-Adamantanol (10.0 g, 65.7 mmol) was added portion-wise. After stirring at rt for 24 h, the solid was filtered-off and the solvent removed under vacuum to yield the title compound (12.3 g, 88%) as yellowish oil, which was used in the next step without further purification. FTIR (cm−1): 2913, 2854, 1780, 1455, 1354, 1152, 1038, 957, 835, 802.

Workup

  1. stirringAfter stirring at rt for 24 h
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-21bbbc4a044648edbf4fd5130f4a9f13
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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