Toluene → HCID 178506415, 화합물

HRID 1370754

반응식

HRID 1370754 반응식
[C:1]1([C@H:7]([C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1.Cl[P:32](Cl)[C-:33]1[CH:37]=[CH:36][CH:35]=[CH:34]1.[C-:39]1([P:44](Cl)Cl)[CH:43]=[CH:42][CH:41]=[CH:40]1.[Fe+2:47]>C(OCC)C.C1COCC1>[C:11]1([C@@H:9]2[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][P:32]([C-:33]3[CH:37]=[CH:36][CH:35]=[CH:34]3)[O:10]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C-:39]1([P:44]2[O:8][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C@@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10]2)[CH:43]=[CH:42][CH:41]=[CH:40]1.[Fe+2:47]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 8471TriethylamineHCID 853019(R,R)-HydrobenzoinHCID 91972168HCID 91972168, 화합물

생성물 1

HCID 178506415HCID 178506415, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

At −78° C., 651 mg (3.04 mmol) of (R,R)-hydrobenzoin is charged in a vessel together with 1.0 ml of abs. triethylamine (6.63 mmol) in 150 ml of abs. toluene. A solution of 425 mg (0.80 mmol) of 1,1′-bis(dichlorophosphino)ferrocene (X) in 25 ml of abs. THF is added dropwise within 2 h. Then, thawing is allowed slowly in a cooling bath over night with stirring. The solution obtained is completely freed from solvent, and the orange solid is taken up in 200 ml of abs. diethyl ether. Insolubles are separated off by filtration through a P4 frit with Celite 545® as a filtering aid. The clear orange filtrate is completely freed from solvent to obtain an orange solid. Analytical results: 1H NMR (d8-THF, 300 MHz): 7.40 (s) [8H], 7.36-7.30 (m) [6H], 7.29-7.23 (m) [4H], 7.22-7.11 (m) [6H], 5.05 (d) JH-P=8.1 Hz [2H], 4.95 (d) JH-P=9 Hz [2H], 4.82-4.60 (m) [8H]; 31P NMR (d8-THF, 121 MHz): 181.7 (s).

후처리

  1. waitThen, thawing is allowed slowly in a cooling bath over night
  2. customThe solution obtained
  3. customInsolubles are separated off by filtration through a P4 frit with Celite 545® as a filtering aid
  4. customto obtain an orange solid
  5. customAnalytical results

출처 및 근거

ORD 기록
ord-7db29df5a770448d83a7d76c6a280285
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583305B1

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