1-Bromo-6-fluorohexane → 2-[(10-Fluorodec-3-YN-1-YL)oxy]oxane

HRID 1263086

반응식

HRID 1263086 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[CH:11].C([Li])CCC.[F:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CCCCCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][F:17]

참가 물질

5

반응물 3

HCID 97651-Bromo-6-fluorohexaneHCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

생성물 1

HCID 204558062-[(10-Fluorodec-3-YN-1-YL)oxy]oxane수율 44%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

Repetition of the procedure described in Example 3 using 0.7992 g (5.06 mmol) of 3-butyn-1-yl tetrahydropyranyl ether, 3.6 mL (5.06 mmol) of 1.39M n-butyl lithium in hexane and 1.117 g (6.07 mmol, 1.2 eq) of 6-fluoro-1-bromo-hexane followed by purification by flash chromatography affords 10-fluoro-3-decyn-1-yl tetrahydropyranyl ether (570 mg, 44%) as a clear colorless oil: Rf=0.58 hexane/ethyl acetate (7:3, v/v); IR (film) ν2850-2950 (alcane CH); and 1H-NMR (CDCl3) δ1.20-1.95 (m, 14H), 2.15 (m, 2H), 2.45 (m, 2H), 3.65 (m, 4H), 4.42 (dt, J=48 Hz, 6 Hz, 2H), 4.65 (br s, 1H).

후처리

  1. customfollowed by purification by flash chromatography

출처 및 근거

ORD 기록
ord-a50e15b3ad6a4e1eaa8b84ece03ca6d5
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04455441

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