Water → HCID 12136223, compound

HRID 857956Notes

Reaction equation

HRID 857956 reaction equation
O.COC1C=CC(C[O:11][C@@H:12]([C@@H:54]([CH3:64])[CH2:55][O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C@H:13]([C@H:15]([O:46][Si:47]([CH3:53])([CH3:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:16]([CH3:45])[CH2:17]/[C:18](/[CH3:44])=[CH:19]\[C@H:20]([CH3:43])[C@H:21]([C@@H:30]([CH3:42])[CH2:31][O:32]CC2C=CC(OC)=CC=2)[O:22][Si:23]([CH3:29])([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:14])=CC=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH3:25][C:24]([Si:23]([CH3:28])([CH3:29])[O:22][C@H:21]([C@@H:20]([CH3:43])/[CH:19]=[C:18](/[CH3:44])\[CH2:17][C@H:16]([CH3:45])[C@@H:15]([O:46][Si:47]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:52])[CH3:53])[C@H:13]([CH3:14])[C@@H:12]([OH:11])[C@@H:54]([CH3:64])[CH2:55][O:56][CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C@@H:30]([CH3:42])[CH2:31][OH:32])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12136222HCID 12136222, compound

Product 1

HCID 12136223HCID 12136223, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Water (3 mL) is added to a solution of (5R,6S,7Z,10S,11R)-11-[(1R,2S,3S)-2-[(4-methoxyphenyl)methoxy]-1,3-dimethyl-4-(phenylmethoxy)butyl]-5-[(1S)-2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disilapentadec-7-ene (1.0 g, 1.19 mmol) in CH2Cl2 (30 mL) at 23° C. and stirred for 5 min. DDQ (1.62 g, 7.14 mmol, 6 eq) is added at once and stirred for 15 min. The product mixture is concentrated. The residue is filtered through celite and washed with hexane. The hexane layers are dried and concentrated. The crude product is chromatographed (from hexane to 10% EtOAc in hexane) to give 630 mg (89%) of the desired compound as a colorless oil.

Workup

  1. stirringstirred for 15 min
  2. concentrationThe product mixture is concentrated
  3. filtrationThe residue is filtered through celite
  4. washwashed with hexane
  5. dry with materialThe hexane layers are dried
  6. concentrationconcentrated
  7. customThe crude product is chromatographed (from hexane to 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-9b6cdece9cad4676865000b48e4a4692
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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