Tetrakis(hydroxymethyl)phosphonium chloride → 2,2-Dimethoxyethylcyclopent-3-enol

HRID 1009095노트

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HRID 1009095 반응식
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][C:5]([OH:12])([CH2:9][CH:10]=[CH2:11])[CH2:6]C=C.[Cl-].OC[P+](CO)(CO)CO>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(O)(C)C.[OH-].[Na+].O>[CH3:14][O:13][CH:3]([O:2][CH3:1])[CH2:4][C:5]1([OH:12])[CH2:6][CH:11]=[CH:10][CH2:9]1

참가 물질

8

반응물 2

HCID 31298Tetrakis(hydroxymethyl)phosphonium chlorideHCID 866141134-(2,2-Dimethoxyethyl)hepta-1,6-dien-4-ol

생성물 1

HCID 673065002,2-Dimethoxyethylcyclopent-3-enol

시약·촉매·용매 5

HCID 178425456HCID 178425456, 화합물촉매HCID 962Water용매HCID 3776Isopropanol용매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 4-(2,2-dimethoxyethyl)hepta-1,6-dien-4-ol (28 g, 140 mmol) in DCM (2 L) was charged to a 3 L RB flask. Dry argon was bubbled through the solution for ˜30 minutes. Grubbs second generation catalyst (5.9 g, 7.0 mmol) was added and the reaction was allowed to stir under argon for 15 hours. The reaction was quenched with a solution of tetrakis-(hydroxymethyl)phosphonium chloride (27 g, 140 mmol) in isopropanol (200 mL) and 10 N NaOH (14 mL), and stirred for 15 hours. The reaction was diluted with water (1 L) and poured into a seperatory funnel. The DCM layer was separated and the aqueous was extracted with DCM (3×100 mL). The combined organics were concentrated to a dark oil which was purified by flash chromatography on a 330 g ISCO column eluting by gradient hexanes to 20% EtOAc/hexanes over a 50 minute period. Product fractions were combined to afford the title compound.

후처리

  1. customDry argon was bubbled through the solution for ˜30 minutes
  2. stirringstirred for 15 hours
  3. additionpoured into a seperatory funnel
  4. customThe DCM layer was separated
  5. extractionthe aqueous was extracted with DCM (3×100 mL)
  6. concentrationThe combined organics were concentrated to a dark oil which
  7. customwas purified by flash chromatography on a 330 g ISCO column
  8. washeluting by gradient hexanes to 20% EtOAc/hexanes over a 50 minute period

출처 및 근거

ORD 기록
ord-2d83a5ed07d74287b7298e1263f209aa
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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