Triphenylphosphine → (+/-)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane

HRID 13914노트

반응식

HRID 13914 반응식
[Si:1]([O:8][CH2:9][CH:10](O)[CH2:11][C:12]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[OH:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:4]([Si:1]([CH3:2])([CH3:3])[O:8][CH2:9][CH:10]1[O:21][C:13]2[C:14]3[CH2:15][CH2:16][CH2:17][C:18]=3[CH:19]=[CH:20][C:12]=2[CH2:11]1)([CH3:5])([CH3:7])[CH3:6]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 68584043(+/-)-5-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol

생성물 1

HCID 68583654(+/-)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol (6.78 g, 21.02 mmol) in tetrahydrofuran (210 mL) cooled to 0° C. was added triphenylphosphine (5.79 g, 22.07 mmol) followed by diethylazodicarboxylate (3.84 g, 22.07 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched by the addition of water (10 mL) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:7) provided 2.93 g (46%) of (±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane as a colorless oil. Rf=0.86 (silica, ethyl acetate:hexanes 1:5); Anal. calcd. for C18H28O2Si: C, 71.0; H, 9.27. Found: C, 69.77; H, 9.21.

후처리

  1. customThe reaction mixture was quenched by the addition of water (10 mL)
  2. customthe solvent was removed in vacuo
  3. customto give a crude solid
  4. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:7)

출처 및 근거

ORD 기록
ord-74af17c71e4c45f0b64a7f4faf47ee5f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728155B2

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