Ammonium Chloride → (R)-(+)-tert. Butyl 2,6-dimethyl-4-heptenyl ether

HRID 1701251노트

반응식

HRID 1701251 반응식
[I-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:3]([CH3:5])[CH3:4].C([Li])CCC.[C:30]([O:34][CH2:35][C@H:36]([CH3:40])[CH2:37][CH:38]=O)([CH3:33])([CH3:32])[CH3:31].[NH4+].[Cl-].C([C@H](O[C@@H](C(C)(C)C)C(C)CC=CC(C)C)C(C)CC=CC(C)C)(C)(C)C>CCCCCC.C1C=CC=CC=1.O1CCCC1>[CH3:40][C@H:36]([CH2:37][CH:38]=[CH:2][CH:3]([CH3:5])[CH3:4])[CH2:35][O:34][C:30]([CH3:33])([CH3:32])[CH3:31]

참가 물질

9

반응물 5

HCID 25517Ammonium ChlorideHCID 12923323(R)-4-tert. butoxy-3-methylbutanalHCID 18386505Isobutyltriphenylphosphonium iodideHCID 131711725(R)-(+)-tert. butyl-2,6-dimethyl-4-heptenyl etherHCID 178418339Butyllithium

생성물 1

HCID 131711724(R)-(+)-tert. Butyl 2,6-dimethyl-4-heptenyl ether

시약·촉매·용매 3

HCID 241Benzene용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매2회

실험 절차

A slurry of 2.67 g. (6 mmoles) of isobutyl triphenylphosphonium iodide in 50 ml. of dry tetrahydrofuran was stirred at 0° C. while a solution of 2.94 ml. (6 mmoles) of 2.04 M n-butyllithium in hexane was added dropwise. The resulting mixture was stirred for 10 minutes and then treated with a solution of 0.475 g. (3 mmoles) of (R)-4-tert. butoxy-3-methylbutanal in 25 ml. of dry tetrahydrofuran. After the addition was complete, the reaction mixture was stirred for one hour at room temperature then treated with saturated aqueous NH4Cl and worked up with hexane in the usual manner. The crude product (0.792 g.) was chromatographed on 25 g. of silica gel. Elution with 9:1 parts by volume hexane-ether followed by evaporative distillation gave 0.418 g. (70.4%) of (R)-(+)-tert. butyl-2,6-dimethyl-4-heptenyl ether as a colorless liquid, b.p. 75°-80° C. (bath temperature) (10 mm Hg.); [α]D25 +11.44° (c 0.61, C6H6).

후처리

  1. additiontreated with a solution of 0.475 g
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for one hour at room temperature
  4. customThe crude product (0.792 g.) was chromatographed on 25 g
  5. washElution with 9:1 parts by volume hexane-ether
  6. distillationfollowed by evaporative distillation
  7. customgave 0.418 g

출처 및 근거

ORD 기록
ord-8c645dbd372b40998f1d58025fdee00e
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04191842

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