Triphenylphosphine → HCID 178501275, 화합물

HRID 1035695노트

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HRID 1035695 반응식
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.O[C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:11][O:10][C:8]([C@H:5]1[CH2:4][CH2:3][C@H:2]([O:1][C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[CH:15][CH:14]=2)[CH2:7][CH2:6]1)=[O:9]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 178501284HCID 178501284, 화합물

생성물 1

HCID 178501275HCID 178501275, 화합물수율 34.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2.20 g of methyl cis-4-hydroxycyclohexanecarboxylate (13.88 mmol, 1 eq.), 2.70 g of tert-butyl 4-hydroxybenzoate (13.88 mmol, 1 eq.) and 5.46 g of triphenylphosphine (20.82 mmol, 1.5 eq.) are placed in 30 mL of tetrahydrofuran at room temperature. 4.04 mL of diisopropyl azodicarboxylate (20.82 mmol, 1.5 eq.) are added dropwise to the reaction medium with stirring. After 3 hours at room temperature, the medium is concentrated to dryness and taken up in diethyl ether. The triphenylphosphine oxide is filtered off. The organic phase is washed successively with sodium hydroxide solution and then with water, dried over sodium sulfate, filtered and evaporated to give a residue. This residue is chromatographed on silica gel, eluting with a gradient of ethyl acetate in heptane ranging from 10% to 50%. 1.6 g of tert-butyl trans-4-(4-methoxycarbonylcyclohexyloxy)benzoate are obtained.

후처리

  1. concentrationthe medium is concentrated to dryness
  2. filtrationThe triphenylphosphine oxide is filtered off
  3. washThe organic phase is washed successively with sodium hydroxide solution
  4. dry with materialwith water, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue
  8. customThis residue is chromatographed on silica gel
  9. washeluting with a gradient of ethyl acetate in heptane ranging from 10% to 50%

출처 및 근거

ORD 기록
ord-941cbb9b38ed4933a067b274588cc97c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546391B2

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