Triethylamine → tert-Butyl-{1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-prop-2-ynyloxy}-dimethylsilane

HRID 1814195Notes

Reaction equation

HRID 1814195 reaction equation
[Cl:1][C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][CH:9]([OH:12])[C:10]#[CH:11].[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[C:18]([Si:21]([O:12][CH:9]([CH2:8][CH2:7][C:6]1[S:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[C:2]=1[Cl:1])[C:10]#[CH:11])([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 219644275-(3-Chloro-benzo[b]thiophen-2-yl)-pent-1-yn-3-ol

Product 1

HCID 21964439tert-Butyl-{1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-prop-2-ynyloxy}-dimethylsilaneYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol 18 (2.20 g, 8.78 mmol) in dichloromethane (15 mL) was treated with DMAP (215 mg, 1.8 mmol), TBSCl (1.59 g, 10.5 mmol), and triethylamine (1.8 mL, 13.2 mmol). The reaction was stirred for 24 h and then saturated sodium bicarbonate solution (50 mL) was added. The mixture was extracted with dichloromethane (2×50 mL) and the combined dichloromethane solution dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (4% ethyl acetate/hexane) gave 3.06 g (6.4 mmol, 73%) of the protected alcohol (19).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  2. dry with materialthe combined dichloromethane solution dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d4d53d8bf8474c50b908a6d84353b307
Source dataset
uspto-grants-2005_04
Patent number
US06875787B2

Reaction notes

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