Hydrochloric Acid → 4-Cyclohexylmethyloxy-2-benzyl-benzoic acid

HRID 363032노트

반응식

HRID 363032 반응식
[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])(CC)C.CN(C)CCN(C)C.C(O)C.N#N.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>O1CCCC1.O>[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 250196894-(Cyclohexylmethoxy)benzoic acidHCID 86585260Nitrogen ethanolHCID 178418400CID 53628100

생성물 1

HCID 536777644-Cyclohexylmethyloxy-2-benzyl-benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-100 °C

실험 절차

A solution of 4-cyclohexylmethyloxybenzoic acid (19-1) (1.00 g, 4.27 mmol, 1 equiv) in tetrahydrofuran (10 mL) was added to a solution of sec-butyllithium (1.3M, 8.21 mL, 10.7 mmol, 2. 50 equiv) and N, N, N', N'-tetramethylethylenediamine (1.61 mL, 10.7 mmol, 2.50 equiv) in tetrahydrofuran (10 mL) at -100 ° C. (ethanol-N2 (l)). The resultant orange suspension was stirred at -100° C. for 1 h, then warmed to -78 ° C. and held at that temperature for 15 min. Benzyl bromide (2.00 mL, 16.8 mmol, 3.93 equiv) was added to the cold reaction mixture, causing the color to change to light yellow. The suspension was stirred at -78° C. for 35 min, then was poured into water (150 mL). The aqueous mixture was acidified to approximately pH 2 with an aqueous 1N hydrochloric acid solution and was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over magnesium sulfate and were concentrated. The residue was purified by flash column chromatography (40% hexanes in ethyl acetate initially, grading to 100% ethyl acetate) to afford the desired carboxylic acid 19-2 as a white solid.

후처리

  1. temperaturewarmed to -78 ° C.
  2. waitheld at that temperature for 15 min
  3. stirringThe suspension was stirred at -78° C. for 35 min
  4. extractionwas extracted with ethyl acetate (2×100 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationwere concentrated
  7. customThe residue was purified by flash column chromatography (40% hexanes in ethyl acetate initially

출처 및 근거

ORD 기록
ord-e330e90d84d34122a94db4c14f1905c9
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872138

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