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Ethyl chloroformate → Tris(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methane

HRID 1450033
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인쇄 미리보기

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HRID 1450033 반응식
[CH3:1][C:2]1([CH3:49])[O:6][C:5]2[C:7]([CH:16]([C:33]3[C:43]4[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=4[CH:41]=[C:35]4[O:36][C:37]([CH3:40])([CH3:39])[O:38][C:34]=34)[C:17]3[C:27]4[O:28][C:29]([CH3:32])([CH3:31])[O:30][C:26]=4[CH:25]=[C:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=34)=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.[Li]CC[CH2:53][CH3:54].[CH2:55]([O:57][C:58](Cl)=[O:59])[CH3:56]>C1COCC1>[CH2:55]([O:57][C:58]([C:41]1[C:35]2[O:36][C:37]([CH3:40])([CH3:39])[O:38][C:34]=2[C:33]([CH:16]([C:17]2[C:18]3[O:22][C:21]([CH3:23])([CH3:24])[O:20][C:19]=3[C:25]([C:11]([O:12][CH2:53][CH3:54])=[O:10])=[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[O:28][C:27]=23)[C:7]2[C:5]3[O:6][C:2]([CH3:49])([CH3:1])[O:3][C:4]=3[C:15]([C:2]([O:3][CH2:4][CH3:5])=[O:6])=[C:9]3[O:10][C:11]([CH3:13])([CH3:14])[O:12][C:8]=23)=[C:43]2[C:42]=1[O:46][C:45]([CH3:48])([CH3:47])[O:44]2)=[O:59])[CH3:56]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 67729115Tris(2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methaneHCID 178418339Butyllithium

생성물 1

HCID 18943071Tris(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methane수율 45.9%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
-60 °C

실험 절차

Tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methane (1.35 g, 2.0 mmol (Example 17)) was dissolved in dry THF (400 mL) under N2, and the temp was lowered to -40° C. and n-BuLi (4.86 mL, 12.2 mmol) was added and the temperature was allowed to rise gradually to 0° C. The mixture was cooled to -60° C., and a solution of ethylchloroformate (4.0, 36.7 mmol) in THF (50 mL) was added. The reaction mixture was left overnight and worked up as described under Example 20 above. The chromatography gave (0.41 g, 24%) of tris(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methane.

후처리

  1. customwas lowered to -40° C.
  2. customto rise gradually to 0° C

출처 및 근거

ORD 기록
ord-be38ea3e18514244bceb92572c0a3ef8
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05599522

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