Bromomethyl 4-methoxyphenyl ketone → HCID 178444638, compound

HRID 1812955Notes

Reaction equation

HRID 1812955 reaction equation
C#CCCCCC=O.COc1ccc(C(=O)CBr)cc1>O=C(O)C1CSCN1.C1=CC=C(C(=C1)C2=C3C=C(C(=O)C(=C3OC4=C(C(=C(C=C24)Br)O)Br)Br)Br)C(=O)O.[Na].[Na].CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(OC)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(OC)cc1

Participants

8

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 79372,6-LutidineHCID 11355455Hept-6-ynal

Product 2

HCID 178444638HCID 178444638, compoundHCID 178444639HCID 178444639, compound

Reagents, catalysts & solvents 3

HCID 9934TimonacicCatalystHCID 124202469Eosin Y disodium salt, analytical standardCatalystHCID 6228DimethylformamideSolvent5×

Conditions

Temperature
22 °C

Workup

  1. aliquot4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  2. addition4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  3. additionchiral resolving regent (150 mM in DCM, 40 uL)
  4. additionCuI with DIPEA (400 mM in ACN) 40 uL
  5. additioninternal standard 1-phenylprop-2-yn-1-ol (4) (25 mM in ACN) 40 uL
  6. stirringNo procedure recorded
  7. aliquotAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate
  8. additionAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate and diluted with 190 uL ACN before the IM-MS analysis

Sources & evidence

ORD record
ord-c49e0cab13a4491a9fe1a0b23de6484d
Source dataset
Dataset from `Ultra-high-throughput mapping of the chemical space of asymmetric catalysis enables accelerated reaction discovery`

Reaction notes

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