7-Nitro-1-tetralone → 7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 74087

반응식

HRID 74087 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

생성물 1

HCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol수율 80.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

7-Nitro-3,4-dihydro-2H-naphthalen-1-one (200 mg, 1.05 mmol) was dissolved in methanol (5 mL) and NaBH4 ((78 mg, 2.05 mmol) was added in portions. The reaction was stirred at room temperature for 20 min and then concentrated and purified by column chromatography (10-50% ethyl acetate-hexanes) to yield 7-nitro-1,2,3,4-tetrahydro-naphthalen-1-ol (163 mg, 80%). 1H NMR (400 MHz, CD3CN) δ 8.30 (d, J=2.3 Hz, 1H), 8.02 (dd, J=8.5, 2.5 Hz, 1H), 7.33 (d, J=8.5 Hz, 1H), 4.76 (t, J=5.5 Hz, 1H), 2.96-2.80 (m, 2H), 2.10-1.99 (m, 2H), 1.86-1.77 (m, 2H); HPLC ret. time 2.32 min, 10-99% CH3CN, 5 min run.

후처리

  1. concentrationconcentrated
  2. custompurified by column chromatography (10-50% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-d1aa63ae2bca493ca883072ad2f521ad
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

연결된 노트

불러오는 중…