Hydrochloric Acid → 7-(1-Adamantyl)-6-benzyloxy-2-naphthylboronic acid

HRID 618480

반응식

HRID 618480 반응식
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17](Br)=[CH:18]4)=[CH:13][C:12]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([Li])CCC.[B:35](OC)([O:38]C)[O:36]C.Cl>C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([B:35]([OH:38])[OH:36])=[CH:18]4)=[CH:13][C:12]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 220003597-(1-Adamantyl)-6-benzyloxy-2-bromonaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 220003137-(1-Adamantyl)-6-benzyloxy-2-naphthylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3 g (6.7 mmol) of 7-(1-adamantyl)-6-benzyloxy-2-bromonaphthalene and 50 ml of THF were introduced into a three-necked flask under a stream of nitrogen. 3.2 ml (8 mmol) of n-butyllithium (2.5M in hexane) were added dropwise at -78° C. and stirring was carried out for 15 minutes, at the same temperature. 2.1 g (20 mmol) of trimethyl borate were added and stirring was carried out for 2 hours. 23 ml of hydrochloric acid (1N) were added at -50° C. and the temperature was permitted to increase to room temperature. The reaction mixture was extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane, filtered and dried. 2.8 g (100%) of the expected boronic acid were collected, which acid was used, as is, in the synthesis to follow.

후처리

  1. stirringstirring
  2. waitwas carried out for 2 hours
  3. extractionThe reaction mixture was extracted with ethyl ether
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas triturated in heptane
  9. filtrationfiltered
  10. customdried
  11. custom2.8 g (100%) of the expected boronic acid were collected
  12. customas is, in the synthesis

출처 및 근거

ORD 기록
ord-f8f190b771e24f069e6cd5ea28924037
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952382

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