Bromomethyl 4-methoxyphenyl ketone → HCID 178444638, compound

HRID 1812987Notes

Reaction equation

HRID 1812987 reaction equation
C#CCCCCC=O.COc1ccc(C(=O)CBr)cc1>O=C(O)[C@@H]1Cc2ccccc2N1.Cc1ccc(-c2cc(-c3ccc(C)cc3)[o+]c(-c3ccc(C)cc3)c2)cc1.[B-](F)(F)(F)F.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 2733920Indoline-2-carboxylic acid, (S)-CatalystHCID 13902521HCID 13902521, compoundCatalystHCID 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-b905058e17d94e708a523283e0d127a4
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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