Dichloromethane → HCID 86602895, compound

HRID 2252496Notes

Reaction equation

HRID 2252496 reaction equation
[Si:1]([O:8][C@H:9]([C@@H:23]([CH3:35])[CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@@H:10]([CH3:22])[CH2:11][O:12]CC1C=CC(OC)=CC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O>[Si:1]([O:8][C@H:9]([C@@H:23]([CH3:35])[CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:32])([CH3:34])[CH3:33])([CH3:29])[CH3:30])[C@@H:10]([CH3:22])[CH2:11][OH:12])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69215725HCID 69215725, compound

Product 1

HCID 86602895HCID 86602895, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The PMB alcohol 62 (6.11 mmol) was added to CH2Cl2 (19 ML) then H2O (1 mL) and DDQ (1.80 g, 7.93 μmol) were added. After 1 h of stirring, the reaction was quenched by adding saturated aqueous NaHCO3 (100 mL). The organic phase was washed with saturated aqueous NaHCO3 (3×100 mL) and brine, dried over MgSO4 filtered and concentrated. Purification by flash column chromatography (EtOAc/hexane 1:9) furnished 63 (2.23 g, 90%) as a colorless oil: IR (CHCl3) 3403, 2928, 2856, 1472, 1463, 1388, 1256, 1100, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) ε3.59-3.50 (m, 4H), 3.46 (dd, J=5.5, 3.7 Hz, 1H), 1.83-1.75 (m, 1H), 1.62-1.52 (m, 2H), 1.49-1.35 (m, 2H), 1.18-1.05 (m, 1H), 0.91 (d, J=7.0 Hz, 3H), 0.87-0.84 (m, 21H), 0.05 (s, 3H), 0.03 (s, 3H), 0.00 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 80.4, 65.8, 63.3, 38.1, 37.8, 31.1, 29.6, 26.0, 25.9, 18.2, 15.9, 14.9, 4.0, −4.2, −5.4; LRMS (ESI) 427.3 [M+Na]+, 256.8, 212.1; HRMS (ESI) calcd for C21H48O3Si2Na 427.3040 [M+Na]+, found 427.3050; [α]20D−14.0 (c 0.6, CHCl3).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aqueous NaHCO3 (100 mL)
  3. washThe organic phase was washed with saturated aqueous NaHCO3 (3×100 mL) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (EtOAc/hexane 1:9)

Sources & evidence

ORD record
ord-cab20116e19d4cc8bbe411dce67b05fe
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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