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

HRID 13914ノート

反応式

HRID 13914 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-74af17c71e4c45f0b64a7f4faf47ee5f
出典データセット
uspto-grants-2010_06
特許番号
US07728155B2

反応ノート

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