Triethylamine → HCID 68822387, compound

HRID 2378506Notes

Reaction equation

HRID 2378506 reaction equation
[OH:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.C(N(CC)CC)C.[Si:26](OS(C(F)(F)F)(=O)=O)([CH3:29])([CH3:28])[CH3:27].[NH4+].[Cl-]>C1COCC1.C(OCC)C>[CH3:17][CH:15]1[CH2:16][C:2]2([O:1][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:13](=[O:18])[CH2:14]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 25517Ammonium ChlorideHCID 65367Trimethylsilyl triflate2×HCID 67491946HCID 67491946, compound

Product 1

HCID 68822387HCID 68822387, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25 mg (0.1 mmol) of (16) and 17 μl (0.12 mmol) triethyl amine in 0.5 ml THF was treated at 0° C. with 21 μl (0.11 mmol) TMSOTf. After 30 min 8 μl (0.06 mmol) triethyl amine and 10 μl (0.055 mmol) TMSOTf were added. After 10 min the mixture was diluted with diethyl ether and was poured into 2 ml of a saturated NH4Cl solution. The organic phase was separated, diluted with 3 ml of dichloro methane and the solvent was evaporated at room temperature under vacuum to afford 32 mg (19) (yield: 99%).

Workup

  1. customThe organic phase was separated
  2. additiondiluted with 3 ml of dichloro methane
  3. customthe solvent was evaporated at room temperature under vacuum

Sources & evidence

ORD record
ord-04b7df251ca64a62bf580c0e8b8e5216
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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