Pyridine → 2-adamantyl Chloroformate

HRID 233630

반응식

HRID 233630 반응식
[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]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 641492-AdamantanolHCID 94429Triphosgene

생성물 1

HCID 108785372-adamantyl Chloroformate수율 251.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e983796454df48f3abd22062c15dbbfc
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593967

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