tert-Butanol → 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole

HRID 1741387ノート

反応式

HRID 1741387 の反応式
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C(C1[O:67][C:68]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[C:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:70]=1)=C.S([O-])([O-])=O.[Na+].[Na+].[C:89]([OH:93])([CH3:92])([CH3:91])C>O>[OH:93][C@H:89]([C:92]1[O:67][C:68]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[C:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:70]=1)[CH2:91][OH:22]

参加物

7

反応物 5

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 108902322-Vinyl-4,5-diphenyloxazoleHCID 112172021,4-Bis(dihydroquinidine)phthalazine

生成物 1

HCID 569827262-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of AD-mix-β (trade name, Aldrich) (114 g) in a mixture of t-butyl alcohol (400 ml) and water (400 ml) was stirred for 1 hour, and then methanesulfonamide (7.6 g) and 2-vinyl-4,5-diphenyloxazole (20 g) was added to the solution at 0° C. After being stirred for 8 hours at the same temperature, sodium sulfite (50 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by trituration with hexane-ether to afford 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole (21 g). MS (m/z): 282 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 4.03 (1H, d, J=4.6 Hz), 4.90 (1H, t, J=4.6 Hz), 7.2-7.6 (10H, m)

後処理

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by trituration with hexane-ether

出典と根拠

ORDレコード
ord-7eb5a657be424393a1fb816cec409f8c
出典データセット
uspto-grants-1999_10
特許番号
US05972965

反応ノート

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