Water → 2-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-5-((e)-4,4-dibromo-1-ethylbuta-1,3-dienyl)thiophene

HRID 49363Notes

Reaction equation

HRID 49363 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Si:25]([O:32][CH2:33][C:34]1[CH:35]=[C:36]([CH:50]=[CH:51][C:52]=1[CH2:53][O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[O:37][CH2:38][C:39]1[S:43][C:42](/[C:44](/[CH2:48][CH3:49])=[CH:45]/[CH:46]=O)=[CH:41][CH:40]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].O>ClCCl.[Zn]>[Si:25]([O:32][CH2:33][C:34]1[CH:35]=[C:36]([CH:50]=[CH:51][C:52]=1[CH2:53][O:54][Si:55]([C:58]([CH3:60])([CH3:59])[CH3:61])([CH3:56])[CH3:57])[O:37][CH2:38][C:39]1[S:43][C:42](/[C:44](/[CH2:48][CH3:49])=[CH:45]/[CH:46]=[C:20]([Br:24])[Br:21])=[CH:41][CH:40]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88011784HCID 88011784, compound

Product 1

HCID 880114512-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-5-((e)-4,4-dibromo-1-ethylbuta-1,3-dienyl)thiophene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

770 mg (11.7 mmol) of zinc, 3.09 g (11.7 mmol) of triphenylphosphine and 3.9 g (11.7 mmol) of carbon tetrabromide are stirred for 30 minutes at room temperature in 150 mol of dichloromethane. A solution of 3.3 g (5.9 mmol) of (E)-3-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}pent-2-enal (described in Example 7(c)) in 30 mL of dichloromethane is then added dropwise. After stirring for 1 h at room temperature the reaction medium is treated with water and extracted with dichloromethane. After purification on silica gel (eluent: 95 heptane/5 ethyl acetate), the desired product is obtained in the form of a brown oil (m=3.9 g; Y=93%).

Workup

  1. extractionextracted with dichloromethane
  2. customAfter purification on silica gel (eluent: 95 heptane/5 ethyl acetate)

Sources & evidence

ORD record
ord-99c6d6addb954087a7bd32ee8fc34244
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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