Acetyl chloride → HCID 58168596, compound

HRID 1255271Notes

Reaction equation

HRID 1255271 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Si:5]([O:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH2:20][CH2:21][OH:22])[S:18][CH:19]=1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].C(N(CC)CC)C>C1COCC1>[C:1]([O:22][CH2:21][CH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][CH2:13][O:12][Si:5]([C:8]([CH3:9])([CH3:11])[CH3:10])([CH3:7])[CH3:6])[CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58168619HCID 58168619, compound2×

Product 1

HCID 58168596HCID 58168596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of acetyl chloride (0.36 mL) in dry THF (3 mL) was added dropwise over 10 minutes to a stirred solution at 20° C. of 2-(4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethanol [Aromatic Intermediate 20] (1.10 g) and triethylamine (1.18 mL) in dry THF (30 mL). The mixture was stirred at 20° C. for 20 minutes and then partitioned between ethyl acetate and brine. The organic layer was dried, filtered and the solvent evaporated under reduced pressure to give the subtitled compound. Yield 1.20 g.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a3d3dd5c26ed485f8d9c295ee87ca5f5
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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