tert-Butyldimethylsilyl chloride → HCID 57705499, compound

HRID 1662488Notes

Reaction equation

HRID 1662488 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[CH:18]([OH:23])[C:19]([CH3:22])([CH3:21])[CH3:20].[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][C:27]([Si:24]([CH3:26])([CH3:25])[O:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([CH:18]([OH:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[CH:12]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 57705999HCID 57705999, compound

Product 1

HCID 57705499HCID 57705499, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 66.13G (0.500 g, 2 mmol) in DCM (10.00 mL) at 23° C. was added tert-butyidimethylsilyl chloride (0.3 mL, 2 mmol), followed by TEA (0.3 mL, 2 mmol) and DMAP (0.02 g, 0.2 mmol). The reaction was then stirred for 16 hours and concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 69.16A as a colorless oil (0.655 g, 96% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9c5bfa45fb954b7c9fcf1a95e13440f3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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