Toluene → HCID 178506415, compound

HRID 1370754

Reaction equation

HRID 1370754 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 178506415HCID 178506415, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7db29df5a770448d83a7d76c6a280285
Source dataset
uspto-grants-2003_06
Patent number
US06583305B1

Linked notes

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