Water → HCID 59350296, compound

HRID 2271393Notes

Reaction equation

HRID 2271393 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]CC=C)=[O:22])[CH:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([SiH3])C=CC=CC=1.O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:29]=1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:12]([O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[C:21]([OH:23])=[O:22])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12752PhenylsilaneHCID 59350294HCID 59350294, compound

Product 1

HCID 59350296HCID 59350296, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Pd(PPh3)4 (23.1 mg, 0.02 mmol) and 3-((allyloxy)carbonyl)phenyl 3,4,5-tris(benzyloxy)benzoate (600 mg, 1 mmol) were dissolved in CH2Cl2 (3 mL) and cooled in an ice bath. To the resulting solution was added phenylsilane (216 mg, 2 mmol). After stirring for 15 min, H2O (5 mL) was added dropwise, resulting in a precipitate. The solid was washed successively with ethyl acetate, dichloromethane, and water. The combined organic layers were concentrated in vacuo to half-volume and extracted with water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (378 mg, 68%).

Workup

  1. temperaturecooled in an ice bath
  2. customresulting in a precipitate
  3. washThe solid was washed successively with ethyl acetate, dichloromethane, and water
  4. concentrationThe combined organic layers were concentrated in vacuo to half-volume
  5. extractionextracted with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74fc1bd356b6430c9d51aa2b4b324cd6
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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