Chlorotrimethylsilane → HCID 21474481, compound

HRID 1756439Notes

Reaction equation

HRID 1756439 reaction equation
C1COCC1.C[Si](Cl)(C)C.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].I[C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1>[Zn].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.O.CN(P(N(C)C)(N(C)C)=O)C>[C:16]([O:15][C:13]([CH2:12][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 120854-Iodobenzoic acidHCID 79177tert-Butyl bromoacetate

Product 1

HCID 21474481HCID 21474481, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
40 °C

Procedure

11.4 g (0.170 mol) of powdered zinc and 50 ml of THF are-introduced into a three-necked flask, 2.2 ml of trimethylsilyl chloride are added and the mixture is stirred for 15 minutes, 28 ml (0.174 mol) of tert-butyl 2-bromoacetate are then introduced dropwise and the mixture is stirred for 30 minutes. It is cooled to 0° C. (icebath), 5 g (4.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 10.8 g (43.5 mmol) of 4-iodobenzoic acid and 50 ml of HMPA are introduced and the mixture is heated to 40° C. for one hour. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and ethyl ether (95:5). After evaporation of the solvents, 8.1 g (80% ) of the expected product, melting point 132°-133° C., are collected.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. additionare introduced
  3. extractionthe mixture is extracted with ethyl ether
  4. customthe organic phase is separated after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column
  9. washeluted with a mixture of dichloromethane and ethyl ether (95:5)
  10. customAfter evaporation of the solvents, 8.1 g (80% ) of the expected product, melting point 132°-133° C.
  11. customare collected

Sources & evidence

ORD record
ord-bee08751d21849c8a1879da26a27c4c3
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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