Pyridine → 2-adamantyl Chloroformate

HRID 233630

反応式

HRID 233630 の反応式
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[OH:11])[CH2:8]2.[Cl:12][C:13]([O:16]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.N1C=CC=CC=1>ClCCl>[Cl:12][C:13]([O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:16]

参加物

5

反応物 3

HCID 1049PyridineHCID 641492-AdamantanolHCID 94429Triphosgene

生成物 1

HCID 108785372-adamantyl Chloroformate収率 251.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-adamantanol (10.1 g, 66.5 mmol) in dichloromethane (200 mL) was cooled in an ice bath. Bis(trichloromethyl)carbonate (triphosgene) (7.55 g, 25.4 mmol) was added followed by dropwise addition of pyridine (6.2 mL, 77 mmol) at such a rate that the temperature remained below 20° C. After a further 10 minutes the mixture was warmed to room temperature and stirred for a further 2.5 hours. The dichloromethane was removed in vacuo without heating and the residue slurried with ethyl acetate (50 mL). The pyridinium hydrochloride was filtered off and the filtrate evaporated to dryness without heating to yield 2-adamantylchloroformate (76) (13.7 g, 96%); δ H (300M Hz, CDCl3, 1.48-2.32 (14H, m, adamantyl), 5.01 (1H, t, J 3 Hz, adamantyl 2-H); (lit. ,2 δ H (CCl4) 1.3-2.4 (14H, m), 4.95 (1H, s).

後処理

  1. customremained below 20° C
  2. customThe dichloromethane was removed in vacuo
  3. temperaturewithout heating
  4. filtrationThe pyridinium hydrochloride was filtered off
  5. customthe filtrate evaporated to dryness
  6. temperaturewithout heating

出典と根拠

ORDレコード
ord-e983796454df48f3abd22062c15dbbfc
出典データセット
uspto-grants-1997_01
特許番号
US05593967

関連ノート

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